A Beginner’s Guide to On-Line Dating From a Guy’s Perspective


Dating has changed drastically since it was invented by the Greeks (I’m guessing since they’re so romantic!).  Traditional dating began with the father of the male cutting a deal with the father of the female about if their kids were a good match.  It was basically a business arrangement and consisted of families merging together to benefit everyone involved 1.

During the last 30 or so years, dating has evolved into more of a delicate procedure during online-dating-detail-computer-keyboard-purple-double-sized-key-marked-white-heart-text-concept-35845668which a member of one gender would weed out members of the opposite gender that they felt weren’t marriage material.  During the last 15 years or so, people began becoming more career oriented and less family oriented.  They pursued education and employment before starting a family and woke up one morning at 30 something realizing that they weren’t getting any younger but were still single.  Their jobs didn’t allow for much time to meet other members of the opposite gender and as a result many found their situations hopeless.  The blending of generational changes developed into one specific brand of dating service that provided assistance to all types of potential daters: on-line dating.  It was almost like grocery shopping.  Potential dating matches were organized into systemized rows.  One could discover more about their potential match while they were in the comfort of their own homes than they ever would during an awkward 10 minute face-to-face conversation 1.

match-com-couponsThe first online dating service, Match.com, was formed in 1995 and for the first 7 years had a total of 26.6 million people registered 1.  As other internet dating services sprouted up, a trend began.  Dating services were at first very simple and only matched people depending on their profiles, likes and dislikes.  However, after 21 years of experience since the internet dating boom, modern sites (such as eHarmony, ChristianMingle, Chemestry and many others) have developed many progressive matching techniques that will match people in more precise ways.  There are even sites that have strict necessities for their members.  For example, Veggiedate.org caters specifically to vegetarians and asks for an acknowledgement of a rigid vegetarian diet before building a personal profile on their site.  In the US, thousands of Internet dating services have been created with one aim in mind: to give the users the independence and fluidity to date who they want and when they want.

My First Experience…

Me at age 18 in 1996

The first time I tried a dating service, I was 18.  I never had a steady girlfriend in high school and things weren’t looking any better in college.  I had run out of options.  It was 1996 and although the internet was well up and running, many people where I lived in Louisiana weren’t plugged in yet.  One day I was sitting in the living room and saw an ad on TV about a dating service.  It was interesting, so I wrote down the phone number and called then up.  They set up an appointment for me the next day and I was so excited!  I had never utilized a dating service and wondered what it would be like having someone else hook me up with a girl so I didn’t have to do all the leg-work!  Would they match me up with my dream woman?  The time came for the appointment and I followed the directions to an office building in west Shreveport.  As I stepped in the front lobby, I was told to have a seat and offered a drink.  Finally, someone came to me and directed me to a room.  I filled out a personal information sheet and a couple of other personality profile forms and waited for a while.

sylvie-vartan-008The door finally opened and a business-like lady sat down in the seat in front of me.  She went over all the information I had filled out and told me in her French accent, “Ve don’t get zat many young peopel like you around here.  You are young!” she assessed me as if I were a risky business prospect.

We talked for about 20 minutes and she asked me what the difficulty was that I had with meeting girls.  Was this a dating service or was I secretly meeting my blind date on Oprah? I thought.  I simply said that I just hadn’t met the right girl and thought that coming to a dating service would open up a good opportunity.  After showing me the prices of matching me up with the perfect girl (if that was even possible) my eagerness turned into dismay.  My pockets weren’t deep enough for the $700 fee of matching me up with my first date!

Mademoiselle Yvette (that’s what I’ll call her) did stay with me and gave me some good advice on how to meet a girl (so now I’m meeting with a shrink?), “Zust go to ze places you love to go to,” she said (I could almost hear an accordion playing in the background by a guy named Jean-Pierre), “Do ze sings zat interest you and at zose places, zere might be a gerl vaiting zest for you.”  She was right and I might have already met the perfect girl for me.

As I walked out of the door and down the hall, I wasn’t disappointed I had come all the way to Shreveport but hadn’t gotten what I had come for.  I did learn a lesson that day though and it wasn’t on how to speak with a French accent.  That night I lay in bed and thought to myself as I had in the past.  I started thinking about girls and knew that one day; I would meet the woman I loved and would marry her.

Getting Back Into the Scene…

00001Now fast forward 15 years in the future.  I was 33 years old and newly divorced after almost 10 years of marriage and a very lengthy separation.  I was also a single father.  I thought that since my separation had lasted almost 1 ½ years and I was through the heartache of the break-up, I was ready to hit the dating scene.  Although it had been 11 years since my first date with my now ex-wife, I still thought I had that spark in me to intrigue a member of the opposite gender.  And so I went on my first date one week after my divorce.  That didn’t work out, so I turned to on-line dating for the first time.

My Current Status…

Currently, I have over 2 years of experience in on-line dating but I am still single (as of November 2017).  To me, success in on-line dating is that after you physically meet, you go on a few dates together and eventually become an official couple, exclusively dating each other in a 100% monogamous relationship.  Using my “vast wealth of experience”, I will now give you, the beginner, a guide to on-line dating.  Looking back, I wish I had this step by step guide to assist me in my failed attempts at finding my mate.  I hope you will be successful where my previous attempts have floundered.

What Is My Status?

22633_436794180102_978076_nBy “status”, I mean are you really single?  How long have you been single?  Within a year?  1-5 years?  Are you divorced, widowed, separated or never been married?  I would hope that you aren’t seeking a relationship if your status is “separated”.  Personally, I would never try and date a woman who was separated.  By law, they are still married and I just don’t go there.

Realistically speaking, it takes about 18 months (1 ½ years) after a divorce (not including the separation) for someone to be ready to enter into a committed, dedicated relationship that leads to marriage.  There’s just something about the human psyche that needs those 18 months to rejuvenate and re-boot.

12407610_1536872813276569_2073653877_nAre you at a place where you just want to test the waters and see if you still have “it” in you?  You just want to find a casual dating friendship where you feel attractive, wanted and needed?  That was me when I first started dating on-line about a month after my divorce.  I was honest with myself and I knew I didn’t want to commit and fall in love.  Eventually I wanted that but at the time, I was nowhere near ready to entrust my heart to someone.  Although my heart was healed from losing the love I once had with my ex-wife, I was far from ready.

man-thinkingIf you are in this phase, you might want to put dating on pause and give yourself some time to figure things out.  This is the time where you don’t want to rush into dating again.  Find yourself again and discover ways to enrich your life.  Identify who you are as a single person and get used to living your life that way.  Become comfortable in your own skin again.  Instead of using “we”, get accustomed to using “I”.  One of the biggest mistakes you can make is to think you’re ready to date when you aren’t.  There are a lot of people out there who are on a different playing field than you are who want to commit and move to a courting relationship that will lead to marriage.  If that scares you then don’t get into dating just yet.  It’s not fair to those other people who are ready.

That’s what I did.  After meeting 5 or so women and going on several dates with them with nothing working out, I finally realized that I just needed to take some time.  After about 18 months, I was completely ready to dedicate myself to a woman and completely give my heart to her.

Why Choose On-Line Dating?

Still with me here?  If you passed the first question and are ready to move into a man-computer-work-at-homecommitted relationship, ask yourself this question: why choose on-line dating?  Am I stuck in a job that doesn’t give me much of a chance to meet a match?  Is my schedule so rigid that I have little time to meet up with someone?  Where else can I meet someone without using my computer?  Where can I meet someone who is similar and like-minded?

Work is one of the easiest places.  You’re there on an average of 40 hours a week.  You have the most opportunity to meet a match during your down time.  Where else can you meet like-minded people?  Church?  The gym?  An underwater basket weaver’s rally?  An international gathering of people with red hair?  Go to the places that make you the most happy and you will naturally find other’s who like the same things (thanks Yvette!).

Are none of those options working?  Well, you might be a candidate for on-line dating.  Even if you are very active and fulfilled, on-line dating offers something those other activities don’t.  You will meet people on-line that you would have never met before.  It opens the door of opportunity and broadens your horizons in a way that few other options can.

Which Dating Site Should I Choose?

stock_photo_of_travel_journey_5_167845   There are two types of on-line dating sites.  Those you have to pay for and those that are free.  What I’ve learned is that if I want the full experience from a site, I pay for it.  The one’s that say they are free really aren’t unless you try “Plenty of Fish”.  Most “free sites” won’t let you communicate with your match unless you are a paying member.

The on-line sites I have been a subscribing member to are eHarmony, OKCupid, Christian Mingle, Match and Single Parent Meet.  Although each site is unique in its own way, they all offered me ways I can communicate with a potential match.  If I was feeling particularly reluctant, I could send a “smile”, a “wink” or “like” one of their pictures.  If I was really interested, I sent them an e-mail or just write a quick little note.

There are also several sites that are more specific if you want to find a like-minded match: www.farmersdatingsite.com, www.fitness-singles.com, www.LARPpassions.com (you know those people who dress up like Medieval warriors and fight each other with Styrofoam swords?), www.redneckmeet.com and many more.

dating-sitesIf you want to find the best site for you, do a google search and read the reviews.  Do a trial membership and see if you like the layout and what they have to offer.  Most sites offer a subscription for a minimum of 3 or 6 months.  Sometimes you have to pay the fee all up front and sometimes they’ll charge you monthly.  Once you become a member, make sure you know the exact date you signed up so when the subscription runs out, you can cancel.  Otherwise, the site might charge you for an additional 3-6 months!  Always read the fine print!

Building Your Profile

The Profile Picture

bg_player_profile_default_bigYour profile picture is the most important part of your profile.  Many people go wrong when they post their profile picture.  Your profile picture is the first thing a potential match is going to see about you.  They aren’t going to waste their time on seeing what college you went to, if you like cats or if you have kids.  That stuff comes later.  You’ve probably heard the saying, “Don’t judge a book by its cover,”  A potential match is going to look at your profile picture and judge on whether to open up your profile or to continue looking for a better one.  Make your profile picture the first impressive element of your profile.  Make it stand out.  Give it your up most attention!  You may be the perfect match for someone out there but if you don’t have a good profile picture, that perfect match might pass you by.

A picture taken 2 years ago (left) compared to a picture taken last week (right)

Another important part of your profile picture (and other pictures for that matter) is to choose pictures that have been taken within the last year or so.  It’s deceiving to see someone you really like because of their profile picture and realize that you also like who they are, their personality and everything else about them.  Then you meet them and realize that they have gained 40 pounds since their pictures were taken – this is called “catfishing”.  Catfish are known to hide in holes on riverbanks.  They stick their heads out just enough but you can’t see their body.  I am not vain and looks are only the tip of the iceberg.  Someone might be absolutely gorgeous but have a terrible temper.  Or someone might not look very appealing to me but have an amazing character.  You can never tell this unless you meet in person.  That is one of the drawbacks of on-line dating – someone may be totally different in real life than they are on-line.  I am attracted to certain women and there is nothing wrong with that.  It’s my opinion.  I have to be physically attracted to someone if I want to meet her, date her and eventually marry her.  Physical looks and what you’re attracted to are a very important first step before digging deeper into who someone is.

The do’s and don’ts of a profile picture


  • Make sure the lighting is adequate – not too bright but not too dim
  • A potential match doesn’t want to guess if you have a cone-head or wonder if you’re really that ugly if the lighting is too dull
  • A potential match also doesn’t want to wonder if you truly are bald or if your head is just the same color as the background of the picture because it’s too bright


  • Make the picture a bust – only from your shoulders and up – like an ID cardbad-dating-profile-pics-00072
  • A potential match is first interested in your face
  • No full body shots; you can include a full body shot in your other pictures

Facial Expression

  • A natural looking smile is a more attractive face
  • Don’t smirk or show some goofy look to reveal your kooky side

What to wearUntitled

  • Do not and I repeat do not wear sunglasses or a hat
  • A potential match wants to see your real eyes and hair
  • A person can look totally different without their sunglasses


  • Choose a neutral colored background or something simple
  • Be the only item in your profile picture
  • Nobody wants to see your cute little cat in your arms, your best friend next to you (and have to guess which one is you) or worse yet, a bathroom fixture
  • Selfies are okay but do not take a bathroom or a car selfie
  • Your potential match doesn’t want to see what kind of cell-phone you have in a mirror shot or that your bathroom towels are the color of egg-plant

Other Pictures

terranea-5These are the pictures where you show off who you are and what you love to do.  Show a picture of you snowboarding, going on a hike, skydiving or riding your bike.  It seems like the latest craze for these pictures in female profiles is doing hand-stands on paddle boards, pics with Machu Picchu in the background, pics of them kissing their dog or pics of them wearing those fake CGI flower wreaths.  Don’t show or reveal your body too much.  As a Christian guy with morals, the BIGGEST TURN-OFF for me are pictures of a lady showing off certain parts of her body as if she were a Victoria Secret model.  The kind of woman I am looking for is modest, respects herself and is decent enough to not flaunt her body for men to ogle over.  Another turn-off for me is a woman with tattoos.  To an extent, tattoos are okay on women.  A small one on the ankle, inner arm or back.  But when an absolutely gorgeous woman has her arms sleeved or has tats on her chest, it TOTALLY makes her look like a biker chick and de-womanizes her.  How feminine is that?

Again, show plenty of pictures without your sunglasses on.  You may look different in different situations than your profile picture and this is a great place to reveal who you really are without sunglasses.

It’s up to you but you may or may not want to include pictures of your kids.  I’ve seen many ladies post pictures of their kids and blur out their faces.  There is a potential for a sicko out there to see pictures of your kids and do who knows what.

Writing a Summary About Yourself

captamerica-fullsize-datingprofileThis is the part where you get to tell your potential match all about yourself.  Some dating sites make this easy with a questionnaire.  However, it is still very beneficial to give a summary of who you are and what you’re looking for.   Be original and don’t lie or exaggerate.  However, make your summary stick out from among the others.  Everyone okcyogawants to go to Hawaii.  Everyone is a traveler.  Everyone likes the outdoors.  Everyone is looking for their soul-mate or partner in crime.  Everyone likes long walks on the beach.  Clichés are boring.  How well do you know yourself?  You have permission to brag about yourself here and write a story about your character.  If you’re not too into writing, here’s a template example of how to write about yourself:

[About you…]

Write about who you are: a single father/mother, a student, a skydiver: what drives you.  Talk about your hopes: if you’re optimistic, a good listener, how you’ve grown in your experiences, what your beliefs are concerning certain topics you find interesting.  Don’t write too much about your hobbies/pastimes.  Most dating sites have a separate section to include these.  Talk about what the most important issue that drives you and why you believe in them so strongly.  Are you a romantic?  What are your values?  Are you compassionate?  What do you think about communication?  Do you believe in soul-mates?

[About your match…]

This is where you include the traits, values and characteristics you want to see in a potential match.  Does your match have to share your faith?  Does their race/ethnicity matter?  Many dating sites will have a section where you can answer questions about what you’re looking for in your match.  However, this is a section where you can express yourself outside the boundaries of a fact sheet.

Do you want someone who has kids?  Does it matter how long it has been since they were in a relationship?  How long have they been divorced?  This is very important!  I’ve run across women who were freshly out of a divorce or relationship and thought they were ready.  However, it turned out that they were still in the healing stage.  There is nothing more disappointing for me than to get close to someone who is still working through a break-up.

Do you want someone who is enthusiastic, energetic; someone who you can enjoy your hobbies with?  Are you looking for a relationship to complement your life, not just to fulfill or “complete” it?  Are you looking for someone who is not looking to be taken care of but rather who is realistic about the hard work it takes to build and maintain a stable and satisfying relationship?  What about their emotional stability?  Strengths?  Are they honest about life?  Is love expressed through actions more than words?  Are they grounded and have a strong sense of identity, purpose and independence?  Do they demand respect and make a good impression on others?  Do you have to be attracted to them physically?

[About the relationship…]

If you have kids of your own, it makes sense to welcome anyone else who also has kids but who understands the dynamics of blending a family together and the additional issues that come with it.  If you want to read further on blending a family, Ron Deal is a family psychologist who has many resources on blended families.  Are you open to having more kids?

What kind of relationship are you looking for?  Do you just want to see if you “still have it in you”?  Are you looking for something long-term that may lead to marriage?  Do you want to just “date around”?  There are many relationship “fields”.  Make sure you define exactly what you are looking for in a relationship so a potential match can make sure theirs is aligned with yours.  There is nothing more devastating than to get in to a relationship and then realize that you want something totally different than your match does.  These are things that should have been talked about during the beginning stage…like right here!

If you’re still clueless as to what to include in this section, take a personality profile test.  PlentyOfFish.com has a great profile test with 100 or so questions.  It will show who you are and who you are looking for.  Don’t make this section too short but don’t make it too long either.

Other items

Depending on the dating site, the rest of your profile should be easy to complete.  There will be other questions or phrases you can write about yourself but it shouldn’t take that much creativity.  Look over your profile often so you can pick out inconsistencies, mistakes or areas you can revise.  Have a friend of the opposite gender (who is not interested in you) look over your profile and make suggestions.  After you have completed your profile, give yourself a pat on the back!  That was some hard work!  Now take a break and go fishing or something!

Searching for Your Match

Beautiful redhead woman using smartphoneNow that you have your profile completed, you can browse through other’s profiles to see if there is anyone you match with.  Most dating sites have a section where you can fill out search parameters such as age, height, hair color, religion, education, distance and such.  After checking what you want, hit the search button and away you go!  Don’t get overwhelmed at the enormity of match results.  Give yourself some time to look them over.  Grab a cup of coffee and sit in a quiet place.  Critique their profiles and maybe you’ll see something that will cause you to revise your own profile.  Narrow your search down to potential matches.

What I did was make a priority list.  First, they must be a Christian.  Secondly, they had to live within a certain distance from me.  I’ve been in a long-distance relationship that lasted for almost 3 years and it didn’t end well.  Next, I make sure if my potential match is open to me having kids.

I will say that I have seen many women who would have matched well with me up to this point.  However, they included on their profile that they didn’t want to date a man with kids.  If you are over 30 and include on your profile that you don’t want your potential match to have kids, you are seriously limiting yourself!!!  I tried (but failed) to find the statistics on the ages of single parents.  However, the majority of parents (married or unmarried) are over the age of 30.

I Like You!

i_like_you-t2Once you have found potential matches that fit your criteria, you can get to work.  Look over each profile thoroughly.  Make sure you haven’t missed anything like they live on Mars or they believe in the Spaghetti god.  There might be something in a profile that turns you off that you haven’t seen when you just perusing through it before.

Here’s what I did when I found someone I really liked.  I made a list of things they mentioned in their personal summary that stuck out to me like they exercised every day or they were dedicated to God or they loved hiking.  If I was feeling especially brave, I’d write a note to them.  I asked myself, “Would I rather someone ‘like’ a picture or send me a ‘wink’ or a ‘smile’?  Or would I rather someone write a nice letter to me saying how much they liked my stellar blue eyes or that I seemed like a great father?”

Some days, you might just be in the mood to send a smile or a wink.  I will say here that from experience and as a guy, women really like us to take the lead and not be shy.  Things might move on much quicker if you send an actual message.

You Like Me!

Remember writing this in junior high?

After you have sent out your smiles, winks or letters, call it a day.  Take a walk.  Watch a movie.  Take up juggling.  The next day, check your e-mail, open the app or log into the dating site.  If all goes well, you will receive some answers back on your hard earned work.  Some days, you might not get anything but don’t be discouraged.  Some people take longer than others to respond back.  Or they saw your proposal and just thought you didn’t match well with them (or that you were a psychopath – whereas you would go back and revise your profile!).  I’ve found that there are seasons in On-line dating.  For instance, some weeks, I’ll receive several answers back from my e-mails, whereas other times, I’ll go a month of sending out several e-mails per week and not receive anything back.

You might receive one response or more than one.  In the case of one response, the best action to take would be to start slowly.  Take things lightly.  Don’t tell them your life story.  Instead ask questions about them.  Don’t ask to meet up just yet.  I usually gave about a week or so of constant communication before I think of meeting someone in person.  However, I don’t want to just have a pen-pal.

Don’t reveal too much of yourself during the first part of communication.  If you have lived in 6 states before you turned 12, don’t say that.  Just say you’ve moved around a lot.  If you received a medal of valor for saving a drowning kid, restrain yourself.  Just say you like to go swimming.  Those stories might come up when you meet in person.

If things have gone this far, you and your potential match are probably intrigued with each other.  This is the stage of unknowns though.  Don’t count on or expect anything to work out just yet.  Don’t daydream about your first date either.  You might exchange a few messages with 15 people but only 1 might work out.

What if you receive replies from 4 different potential matches who you have sent letters to?  Get to know each of them.  This is where taking notes comes in handy.  The worst mistake you can make is to repeat something to someone thinking that you said it to someone else.  Or that you recall something they said but another one of your potential matches actually said it.  In a perfect world, you will end up with all of your matches and live a blissful polygamous life.  But in reality you’ll only end up with one…or none.

Should I become Facebook friends with them?

add-as-friendThis is something I read about and experienced on my own.  My answer would be no: not right away.  I made the error of asking a woman a few days into our communication if she wanted to “friend” me.  She said no because she wanted to get to know me better first.  Then I asked another woman to “friend” me after our first day of communication and she did.  Everyone is different.  Some people are more cautious than others.  It may be that they have kids and want to protect them or it may just be their nature.  I wouldn’t bring up the Facebook proposal until you know you are comfortable with the other person; whether that be a day or a month.

Meeting in Person

celluloid-is-an-old-ideaAfter you have communicated with someone for a comfortable amount of time (I usually give it at least a week), ask them if they would like to meet in person.  You can’t go on talking indefinitely to someone unless you never want to meet them or they live on Mars.  If they do want to meet up, you have been successful thus far!  If they never write to you again, don’t be too hard on yourself.  They might have just not seen any future in the two of you.  Or they might have been called up to become a deep-sea explorer.  In that case (if you’re patient enough), take scuba-diving lessons and wait for their return.

Pick a location that is low-key.  A place where you can both sit and get to know each other better.  Coffee is always a winner.  Unless your potential match is allergic to it or gets flash-backs when they step into a coffee shop because of pulling all-nighters in college.  In that case, get appetizers at a restaurant.  Your first meeting place should be quiet (not a library) with plenty of people around so your potential match will feel more comfortable.  Don’t go deep sea fishing or in-door skydiving or base-jumping for your first meeting.  Save that for your one year anniversary (if your make it that far).

Someone once gave me an idea for a first date: go see a movie and get something to eat afterwards.  If you don’t have any history with that person, there won’t be much to talk about upon your first meet, unless you are long-lost childhood friends.  After the movie, you’ll have about 1 1/2 hours of “history” together and you’ll have something to talk about over ice-cream or (if you’re a vegan) dried kale with sea salt and Italian lemon mineral water.  I’ve never tried this but it seems like a good idea.

nervous_man_approach_anxietyThis will most likely be the first time any of you have been in the physical presence of one another.  You might be nervous.  You might be over-excited.  Anxious, weak in the knees, nauseous, dizzy, woozy, light-headed or queasy (maybe you are coming down with Coal workers’ pneumoconiosis!).  How long has it been since you’ve been on a first date?  Just be yourself because that’s all you can offer.  Wear comfortable clothing but nothing too casual.  I would usually wear nice shorts and a polo shirt to my first meeting (but I wear shorts year-around!).  Don’t wear perfume or cologne.  Save that for a future BIG night out.  Just remember that if you’re feeling a bit uneasy, your potential match is too probably.

Arrive early and wait by the door.  If they’re late, don’t text or call them.  Show them that you are punctual but not impatient.  If you’re a guy, be a gentleman and hold the door open for her.  If you’re a lady, good luck because I can’t help you there!

questions-to-ask-a-girlSo there you are, standing in front of each other.  This will probably be the first time you have heard each other’s voice.  What do you say?  What do you do?  What is the first thing that sticks out to you as you look at them?  Is she wearing a pretty dress?  Did she find the place okay?  Are you glad to finally meet in person?  Does she look delightful?  Express yourself in those ways.  Don’t be too forward but don’t hold back either.

What do you do next?  Do you hug?  Shake hands?  Just stand there?  I’ve done all three and I’ll tell you what worked.  I shook hands with one woman and it seemed too impersonal.  Kind of like we were business associates meeting to discuss quality management.

I hugged another woman.  We had been communicating for about a week and found that we had a lot in common.  Our conversations on-line were very lively and we really connected.  We were very open with one another and it felt awkward if we wouldn’t have hugged.

Another time (with another woman), I just stood there (not awkwardly) and said something to the effect that it was nice to finally meet her.  I then motioned to her if she wanted to go first to order something.

Another time with another woman, after holding the door open for her, I made a move as if to hug her.  When she didn’t follow through with the same motion, I was already half-way into the hug and I was screwed.  I ended up patting her on her back.  Yes, it was very awkward!  And we didn’t work out…go figure!

If you’ve been to this establishment before, order something you never have.  You can talk about it later!  It doesn’t matter who orders first but if you’re a guy pay for your date!  That is the one key item she will be looking at to see if you are a true gentleman.  Again, if you’re a lady, I can’t help you here.  But if I were one and my date didn’t pay for me, I’d be looking for a quick way out of there!

Now you’re sitting at a table (facing each other) with your drinks or maybe you got some appetizers (hopefully it’s not lengua de vaca – AKA cow tongue!).  What do you say?  If you’re good at conversation, it shouldn’t be too difficult.  Just pretend that you’re meeting someone in the lunchroom at work for the first time…only don’t talk all about your work because this meeting is different.

You can build on things you already know about them.  So she was born locally?  Which 195944part of town did she grow up in?  Is her family here?  Did she know that coffee was first discovered in Ethiopia by a goat farmer?  Don’t try too hard to be someone you’re not.  Remember, she is still trying to figure out if you’re a psycho or not.  Don’t talk too much about yourself and keep the conversation flowing.  If she stops responding to what you’re saying, change the subject (or make sure she’s still breathing!).  Even if you’re not interested in knitting like she is, ask her where she buys her supplies.  What was the latest item she made?  Really?  My grandmother knits too!  Great!  You’re catching on!

From what I’ve experienced, this first meeting can last from 30 minutes to 2 ½ hours.  You’ll know within that amount of time if you’d like to keep seeing this person.  First impressions are usually a good indication of who this person is (unless they are a robot being remotely operated like in the movie Surrogates!).  They will also get a pretty good idea of the same and hopefully you have disproved her view of you as being a psycho.

If she’s a psycho, just tell her you have to use the bathroom and stay in there.  The first person who comes in after you, pay them $5 to see if your date has left or not.  If no one else arrives in the bathroom, hopefully the bathroom has a window that you can climb out of.  Otherwise, you’ll be in there until the store closes.

If you haven’t figured out by now, my second language is sarcasm and the above paragraph 7f587a20264c3c87584dc234742ceb54should not be taken seriously!  As you walk out with your date, open the door for her and give your goodbye respects.  This might entail a hug (if you feel inclined and hopefully she does too!) or a simple wave accompanied by something to the effect of, “It was really great to meet you!  I had a good time!  Let’s keep in touch and do something again!” To which she will do one of the following: hug you back, smile and wave back at you, slap you or say something under her breath like, “I hope I never see that psycho again!

Here’s something I’ve done with every woman after I met her for the first time.  As I was walking back to my car, I would look back at her and wish that we would work out.  I like to get another glimpse at my match to see if she would look back at me too.  However, this has not happened yet.

Do You Want to Meet Again?

Women are very different than men, if you haven’t figured that out already.  They look for leadership, initiation, guidance and confidence.  Unless a woman is really interested in a guy, they will wait for him to initiate the next conversation.  For some women, it is best to wait for that next conversation the day after your first meeting.  She might need some time to sort through some things.  To get a perspective on how things went during your meeting.  If you text her right after you get home from meeting her or a few hours later, she might think you’re smothering her.  I know this from personal experience!  Instead, give her the space she needs.

waitingYou might also need that time to do the same.  That extra day will give you perspective and a chance to think things through without reacting too quickly.  Ask yourself:

How did it go?  Did I feel any chemistry?  Did I do a victory dance at the stop-light on the way home?  Did I think of her often during the rest of the day?  Can I envision myself seeing more of her?  Are my feelings the same today as they were yesterday? 

If the answer to all those questions is a definite “yes”, then at least one of you is ready to move on to the next step.

Maybe you saw your meeting more like “spending time with a long lost friend” or “catching up with a cousin or a sister you haven’t seen in a while” or “meeting with a coworker”.  If that is the case, you probably shouldn’t continue seeing her.  Sad as it may be, most on-line dating encounters end this way.  Well, they have for me anyway.

So is there a way to know what your potential match felt about you?  Like I said, give it a day or so before writing back, unless you know she’s ready to communicate that night.  When you do communicate with her, tell her again what a great time you had with her and some of your favorite highlights of your meeting.  If she also comments and seemed to enjoy herself, you’re on your way to asking the next question: Do you want to meet again?

Image result for second date quotes

The Second Date

If you are ready to move on to the next step, then ask her out again.  First ask yourself: why am I interested in her?  Is it her looks alone?  If that’s the case, shut it down right now because things are going to fail in the future.  Is it her personality?  Is she charming?  Can you see her as the future step-mother of your kids (if you have any)?  And no, it’s not too early to ask that question.  Its always good to think ahead.  You might have already gone through these questions in your head; and if so, you’re on the right track!

second-date-danger-zone-largeWithin the next few days after your first meeting, ask her out again.  Hopefully she says, “YES!” but if she doesn’t, don’t take that as a failure on your part.  Some women just aren’t ready to take on a real man!  So if her answer is yes and if you’ve already gotten this far, this is called success!

Within the year that I last tried on-line dating, I got to the second date with only one out of the eleven women I met!  That’s less than a 10% success rate just for a second date!  So looking back, I know how it feels when a woman says no to the second date.

For this date, do something physical.  I’m not saying to take MMA lessons or go four-184099-850x540-walk-in-the-parkwheeling.  Walk down the beach or around a park.  Go on a leisurely bike ride on a bike path (wearing helmets!).  Don’t go out with another couple or to one of your homes.  Go to a place where there are still plenty of people but where you guys can have some privacy to interact.

You guys already know a little about each other, so this time, expound on that knowledge.  Ask her about her childhood, about college, who her best friend was when she was growing up.  This is not a time to ask about past relationships or marriages unless you guys have grown to that comfort level.  Both of you will be scrutinizing each other and figuring one another out still but by this time, most of the doubts and fears will have faded away.

Before you guys part ways, remember to plan to meet again.  Like I said before, if you’ve already gotten to this point in your friendship, odds are you’ve gotten past the first obstacle: growing comfortable with each other.

Meeting for a Third Time

61054541This should be the time when you ask her out on an official date.  Call her up and let her know you want to go out.  Hopefully she’ll agree!  DON’T and I mean DON’T text her!  Show her that she means more to you and you’re willing to be a man and ask her out!  Wear something nice but not too formal.  Put on some nice pants and a button up, long sleeve shirt.  Go to the movies or go see a play or a musical.  Plan to take her out for coffee or dessert afterwards.  Pick her up in your car but make sure you clean it out ahead of time.  How you present yourself will say a lot about how you treat other people.

Image result for second date quotesIt is during this date that you might be ready to tell her that you want to exclusively date her.  That you like her and want to see things work out with the two of you.  However, those are the hardest words to say.  This is the second hardest obstacle.  You may start by holding her hand or putting your arm around her shoulders.  Look at her body language to let you know how she feels about your advances.  However, above all, you must respect her physically.  Don’t go too far.  A woman’s body is her own and I also believe that it belongs to God.  Her body will also belong to you if you two get married but remember, you’re only on your first official date.  Any upstanding woman will love you so much more if you respect her body, be a gentleman and listen to what she tells you through her speech and body language.

tumblr_o6q5eu97uq1vtb5gdo1_500Make her feel like Cinderella at a ball.  Delight in her and show her that you are strong by controlling your physical desires and by your confidence.  Put in some humor here and there but don’t overdo it.  Too much humor might make her think that you’re not serious about things.  Too little humor might make her thing that you’re too serious.  Use discretion.  By this point, you should be comfortable enough with her that you’ll know when to say certain things, how to approach topics and how to respond to her.

Moving Forward


If you haven’t let her know by now that you want to exclusively be with her or that you really like her and want to pursue a relationship, you’ll want to do it soon.  She might be looking at other guys to date and if you don’t step up and tell her what is on your heart, you might lose her.  And by tell her, I mean with your mouth.  Women don’t want to hear a declaration of commitment over a text message or even over the phone.  A written letter will do nicely too.  A real man will earn his way to a woman’s heart by being bold, taking a step of faith and being confident but always being the gentleman by respecting her.

Are Kids Involved?

fab118e5f15e0f24653318cf3d1a01969be2cd039e298be903bba1fac402826fDo you have kids?  Does she have kids?  Don’t meet them just yet.  Give your new found relationship some time to grow, flourish and blossom.  Make sure you have a good foundation to stand on before you meet her kids or she meets your kids.  The worst thing you can do to your kids is to constantly bring women into their lives that don’t work out.  It disappoints them and sets a bad example.  “How long should I give before my girlfriend meets my kids?” you may ask.  There isn’t a set time period.  My friend gave it 8 months before his girlfriend met his son.  It all depends on how close you’ve grown together, how comfortable you are with each other and how mature your relationship is.  If you still have doubts or if you’re holding things back from her, it isn’t a good time to bring kids into the picture.  When you two are fully comfortable with one another and feel ready to move on to the next phase, then you can meet each other’s kids.

My experience with this went differently.  I was in a long distance relationship, so she met my kids pretty early on.  But because we lived so far apart, we were able to grow and mature our relationship from that distance without the kids being involved as often.

That’s All Folks…

Well, I hope you’ve enjoyed the Beginner’s Guide to On-Line Dating from my perspective.  Every situation is different and will not be handled in the same way.  However, if you follow these guidelines, I hope you will be well on your way of finding a great match and will be successful where I have not been.  I’ve realized a strange fact.  Whenever I am not successful in something, instead of thinking of myself as a failure, I become the best teacher.  Good luck ladies and gentlemen!


  1. History of Internet Dating Services http://pegasus.cc.ucf.edu/~smathews/history.html



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