25 Lessons Learned About Online Dating

Online dating is so worth it! I've had several long-term relationships, short-term romances, embarrassing moments, near disasters, frustrating dates, funny conversations, and soul-crushing experiences.

I've been through it all; had my ups and downs and can honestly say, I wouldn't trade it for anything and recommend all single guys give it a try.  The roller-coaster ride of online dating makes you nauseous at times.  Sometimes I want to pull my hair out with some of the women I meet (and I'm sure I've driven a few bananas), but it's worth it to meet a keeper.

Here are 25 of my top lessons learned about online dating from over the 10 years I've been off and on dating sites.  What it takes to succeed, myths about online dating, me imparting wisdom, and frustrations.

1. Women read your profile

There's a myth that it's all about your photos and you must be incredibly handsome if you want to meet women.  True, your profile photos are important, but if you're serious about finding a match, a well-written profile is critical.

Even on apps such as Tinder and Bumble, you must write something about yourself.  No woman is turned on by a bio that says "I don't know what to write" or "Just ask."

Your hobbies, passions, interests and even a single word make a difference whether a woman contacts you or not.  Anything that makes you interesting can help spark a woman's interest.

Dating sites back up the importance of a dating profile:

• Words used in a profile were shown to have a 64 - 69% larger impact on a woman’s decision to approach men according to Match.com. 
• Zoosk found writing a description about yourself gets you up to 28% more incoming messages.

Put some time and energy into your profile, and you'll have women starting conversations like this in no time.

2. Lack of effort = lack of results

One of the top lessons learned about online dating is a half-assed dating profile, half-assed messages, and half-assed effort all get half-assed results.  The amount of effort you put into online dating tells women how serious you are about meeting someone.

You can't write "Just ask" in your profile or "Hey" on your messages and expect to do well.  Look at this guy; this is the worst way to start a conversation with women:

The example above is a typical message the majority of men send to women.  Put some effort into your messages.  And it's not only your messages, but your entire profile must also be tight.

If you're on Zoosk, think of a clever username.  On POF?  Be sure to write a headline that stands out and not some cliche like "Just fishing."

I've already mentioned how important the written section of your profile is, but use good (current) photos as well.  OkCupid found people who have pictures of themselves doing something interesting have a 40% higher chance of receiving more messages so ditch the selfies.  Use photos of yourself on vacation, playing an instrument, raising your arms on the top of a mountain after a hike, zip lining, making a delicious meal, or surfing for example. 

Lastly, take time to read a woman's profile before sending a message.  Ask open-ended questions which show you read her dating profile.  I cover this in this blog post: 3 Good Conversation Starters for Online Dating Messages To Women.

Follow the tips above, and you'll stand out on any dating site; guaranteed!

3. Avoid women who are "picky"

When a woman writes, she is "picky" or "refuses to settle" I refuse to message them.  I see these type of comments as a red flag because the phrases mean she is looking for a reason NOT to date you.  The phrase itself is justification for she is single.

Everyone should be picky and not settle, but there's no need to write it on your profile.  Women who write these on their profile; no thanks.  I focus on someone who is friendly, positive, and open.

4. Don't beat around the bush

I was the guy who would drag conversations longer than I should.  The result?  I bored the hell out of women, and they'd move on.

I don't know why I did this; fear of rejection, ignoring the signs a woman is interested, or just plain laziness.  Either way, I changed my approach and turned everything around.  When I feel the "energy" is there, I go for the number.  You should do the same too!

Don't engage in long-winded conversations.  You're on a dating site to meet someone and the longer you wait to ask a woman out, the more likely you'll be seen as a "friend" or even worse, she'll meet someone else.

Women write on profiles they aren't into endless messaging like this:  

One study found there's a "tipping point," where if you wait too long to meet for a date, the chances of success plummet.  I covered what happens if you wait too long to ask a woman out in the blog post, How Long Is Too Long To Wait For A First Date With Women Online? 

I can't tell you how many women I blew it with by becoming an email buddy.  They'd vanish, and it was my fault for dragging conversations.  No more.

I aim to get a woman's number sooner than later.  Life is short, so get their number and meet already.  

5. Cocktails (or coffee) is the best choice for a first date

I took women out for dinner, movies, hikes, farmers markets, baseball games, and even a first date at the San Diego Fair.  These are terrible ideas for a first date.

I stopped that rookie mistake and only take women out for coffee or drinks now.  Nothing else.  Have you ever typed into Google "First Date Ideas?"  You'll find crap like this:

• bowling
• mini golf
• a workout class
• karaoke
• rock climbing
• comedy night

The list goes one.  These are horrible ideas for a first date.  Complete and utter nonsense.

Why?  Because there's nothing worse than meeting someone and the chemistry is nonexistent, and there's no attraction.  A dinner date is very uncomfortable when you don't match up with a woman.  Not to mention, you're paying for dinner.

And how can you have a conversation while huffing and puffing up a mountain or staring at a movie screen?  You can't.  

Coffee or drinks offers a quick way to meet up and make sure you're a match.  You know after sitting down for a few minutes with a woman if you want a second date (and she will too).

Look, people are great on paper (the dating site) and the phone (texting), but real life is very different.  You can't sit there, take your time, and think of a response on a date as you can while texting. That's how you know if there's chemistry; an actual conversation.  Save the "fun" stuff like movies and farmers markets for the second date.

6. Dating sites matching algorithms are overrated.

I stopped relying on dating sites matching percentages long ago.  First of all, some studies found dating site matching algorithms don't work.  The matching percentages you see should be taken with a grain of salt because they don't include the "human factor."

In the end, you need to meet the woman face-to-face to see if sparks fly.  Sure, she may be great "on paper," but you won't know until you sit down and talk.

7. Confidence, confidence, confidence

I hear all the time how you must be super attractive to succeed on dating sites.  That's a crock.  Sure, you should be presentable, but if you're confident, you'll do amazingly well on any dating site. 

Women love confidence.  There's a difference between arrogant and confident.  An arrogant man will boast about what he has while a confident man believes in himself and knows what he wants.  

8. Perfection doesn't exist

Be realistic with what you want in a partner.  You have your preferences, as do I, but if you're looking for perfection, you'll never find it.  Just saying.  Compromising on dating sites is OK.

Take stock of what you want in a partner.  Is it unrealistic?  If so, you may end up lonely and regret bypassing women who were great matches, but you chose not dating them because they weren't perfect.

9. Fakes exist - but it's overblown

Have I encountered fake profiles?  Yep!

Have I had fakes contact me?  Yes, indeed.

I can easily spot a fake profile, bot, or scammer.  Usually, the profile has one photo of a gorgeous woman, has zero written about themselves, and is too good to be true.

They also tend to get you offline quickly with some generic phone number, fake email address, or link to an external site like this:

I don't know why so many people fall victim to fakes.  I don't get it, but it's not as widespread as you read (or think).

I've been on Match for months and have yet to encounter a fake profile.  Eharmony and Coffee Meets Bagel maybe one or two.  POF and Zoosk have a lot of fakes, but they're easy to spot. 

Pay attention, and you'll be fine.  If it seems too good to be true, it probably is.

10. Google and Facebook make good allies

I was able to avert disaster thanks to Google several years ago.  I met this amazing woman on POF and asked for her number.  When she sent me her number in a message, I immediately Googled it.  The search results pointed me to her Backpage ad. Backpage, which has since been shut down, was for Escorts.

Yep, this woman who I was ecstatic over, was a hooker.  I immediately told her "no thanks," and that was that.

The Backpage hooker is an extreme example, but when I get a woman's phone number, I do a quick look on Google and Facebook to make sure she's on the up and up.  I make sure her photos are current, and she's not some criminal.

And don't think women aren't doing this to you because they are.  Here are a few facts about women making sure you're on the up and up:

• Match.com found 48% of women use Facebook to research a man before a first date.
• 38% of singles would cancel a date based on information they found on Facebook.

I discussed that on a previous blog post; How Facebook Stalking Can Wreck Your Date Before It Even Starts.

So be careful what you put on your social media.  Women will cancel a date if they find something off-putting.  Those photos of you trashed with your "boys" or venting about something; take it off your Facebook timeline now.  

11. Your ego takes a hit, but it's OK

You find a gorgeous woman you share a lot of interests and are compatible.  You think, "This woman is perfect for me."  You enjoy the same hobbies and want the same things in life.  She describes her ideal mate, and it's you to a T.  "Great," you think.  Well, bad news; she isn't interested.

She doesn't respond to your message.  Or even worse, you see she reads your message and doesn't respond or unmatches with you and is gone into the online dating abyss.

Sometimes a woman will be kind enough to tell you that you aren't her type.  Take this woman from Match.com who told me I am too short for her and asked if I had single friends who are over 6'0".  I knew I had no shot and wished her luck.   

Rejection sucks, and it's going to happen to you; often.  In the past, I took it personally, and it hurt my ego but those days are long gone.

My approach now is if a woman isn't interested, it's her loss.  When a woman tells me I'm not her type, I'm OK with that and thank her for her honesty.  No harm, no foul.  Focus on women who are interested in you and never dwell or get angry at the ones who aren't.

12. Politics is divisive more than ever on dating sites

I'm not a huge political junkie and have no problem discussing (if it comes up) politics, but am amazed when I see so many women who tell you they aren't interested before even meeting you like this woman:

I live in Southern California, and it's typically "Swipe left if you voted for Trump" or messages like this:

Political beliefs can make you or break you.  Here are a few facts about politics:

• The online matchmaking site It’s Just Lunch surveyed its members about politics and found 50% of single women think dating someone with opposite political views was fine for the short-term but not for the long-haul.
• Zoosk found that 20% of women consider it "important for a potential partner to reveal political party info in a profile..."
• Almost one-quarter of Tinder members surveyed said that "political disagreements would be the number one reason to call it quits with an online match."
• POF found 55% of single women wouldn’t date someone who shared they were a Trump supporter on their profile.

The good news is that women who share your political beliefs find you more attractive.  One study found a woman is more likely to respond to a man’s message if he shares political traits with her.  Here are some other findings:

• Interest in responding increased by 12%.
• Interest in long term dating increased by 16%.
• Actual responses rates were between 8-10%.
• Shared political values increased attractiveness by 9%.

Yep, You are HOTTER when a woman shares your political beliefs.  If you want to share your political views, do it positively.  Don't attack the other say.  There's nothing wrong with saying you're a liberal or embrace "conservative values."  It could give you a boost.

13. Some people have odd deal breakers

Height, job security, smoking, education, kids, etc.  These are standard filters women look at on your dating profile.  A woman's preferences can be evolutionary while others are personal.  

Maybe you're interested in a woman who doesn't want to date someone with children or shares your political choices (as I mentioned above).   The likelihood she will respond is low if you are on the opposite end of the scale.

I don't judge.  We all have physical traits, characteristics and lifestyle choices we want in a partner.  I've had women straight out judge me by my zodiac sign (OK, fine) and worse...my favorite sports team.

Yep, I live in San Diego and have had women tell me "No thanks" because I wasn't a Charger fan. WTF.

One woman went off on me when she found out I have a dog.  She sent a rather harsh message about how dog owners houses smell like dog and how gross it is and a turn-off.

There was no arguing with her.  I took offense and argued with her that I take pride in my house and there's not a hint of dog smell.  Then I realized, "What I am chasing this negative person" and stopped.  Good riddance I say.

You want to judge me by my choice in my sports team or my dog?  Great!  Peace out!

14. Don't chase someone who does not want to be caught

Never make a woman a priority when she sees you as an option.  It's easy to identify that you're not a woman's priority:

• She doesn't communicate with you.
• She's always "busy" when you ask her out and never offers an alternative.
• She "cancels" a date and doesn't offer an alternative.
• She vanishes then sends messages weeks later asking "how are you?"

A woman interested in you will always make time.  You feel the "energy" and know she's into you.  If you ask her out and she's busy, she'll say she's free another day and returns your call or text within a day.

15. Women commit the same crimes they complain that men do

No doubt men lie on their profiles, but women are just as guilty.  Outdated photos, dishonesty about age/height/weight/relationship status, ghosting, no-shows/bails, profile cliches, etc.

Everyone lies, but there are little lies and huge ones.  Several years ago, the study Separating Fact From Fiction: An Examination of Deceptive Self-Presentation in Online Dating Profiles found 81% of online daters lied about their weight, height, or age.  Women are just as guilty about lying as men.

Why do people women lie?  They are trying to present themselves in the best possible way to attract a guy.  Shave a few years off their age, say they're more active than they are, embellish a bit about their lifestyle.  All done to project themselves in the best possible light.  But don't sweat it, it’s not going to be something you’ll notice when you meet first hand.

16. Just ask 

I receive a ton of emails from men asking "when a woman says this on her profile, what does it mean?"  For example, "what does it mean when a woman says she's looking for fun" or "what does it mean when a woman writes no drama on her profile?"

Good grief.  Don't be afraid to ask women questions.  Women are more than happy to answer questions.  If a woman has a blank profile or is vague in her self-summary, I have no problem asking "What are you looking for?"  Guess what?  They always respond.

17. There are interesting characters our there

I've started conversations with professors, lawyers, doctors, bartenders, sailboat captains, entrepreneurs, teachers, fast food employees, office workers, women who pretended to be single (who were married), swingers, women in town on business, a truck driver, and even a woman who was an...ahem...escort which I only found out before meeting because I stumbled on her Backpage ad.  

All walks of life.  All levels of education.  Diverse backgrounds.  I've met some pretty cool women on dating sites.

Online dating opens doors to people you'd never encounter at your job or other aspects of your life.  It's been interesting for sure.

18. It takes time

Nothing happens overnight.  Don't expect to join a dating site and meet your soulmate on day 1.  Like everything, it takes time.

You have to weed through the riff-raff to find a keeper.  Be it first messages, conversations, dates, second dates, etc.  It feels like you're on a hamster wheel sometimes, but that's what it takes to find a great match.

Stick with it.  Don't give up.  You'll get there!

19. Taking a break is good for you!

Taking a break from online dating is OK.  If you suffer from burnout, feel like dating is a chore, and are just going through the motions; it's okay to disable your dating profile for a few days, weeks, or as long as it takes before you're ready again.

Take time off to work on yourself, explore hobbies, reconnect with friends, get your things in order, and work on personal goals.  All the time you devoted to online dating is suddenly free for personal goals.  Look at it as a win!

When you're confident again, go ahead and jump back into the dating pool. Taking a break is a positive.

20. Sometimes you see things differently than your date

There have been times where I felt great after the first date.  I'm talking cloud 9; thinking the chemistry was there, there was great banter, and the "energy" was through the roof.  I was ecstatic because I thought I found the perfect match.

There's only one problem.  The woman didn't see it the same way; she texted me she wasn't feeling it and wishing me luck or worse ghosted me.  WHAT?  It's sometimes deflating.

Sometimes we see things the way "we want" instead of how it really is.  What can you do?  You can get upset or learn from it.  Maybe a little self-reflection is in order.  Pay more attention to the signals and signs. 

21. You aren't owed anything

Women don't owe you anything!  Just because you take the time to message a woman doesn't mean you deserve a response.  Nobody owes you a date.  Nobody owes you sex.

If a woman tells you she's not interested or doesn't feel you're a match, don't be an asshole.  Move on.  Don't feel you have to get the last word in.  You aren't her cup of tea, so get over it.

22. All sites work (if there are female members)

I've been on every dating site you can name and found quality women on every single one of them.  I see men complain how OkCupid isn't as good as it once was, Tinder is for hookups, and POF is a waste of time.  Blah, blah, blah.

Nonsense!  If there are women on the site, it's a great opportunity for meeting women.  If I fail on a dating site, I never point the finger at the site or women; I take it as a sign to tune-up my dating profile or change my approaches in my messages.

Online dating results boil down to this: bad profile + bad messages = bad results.  That's it!

23. Be you

In my early days of online dating, I would tell women how much we had in common, be agreeable, and would respond to messages with what I thought women wanted to hear.

Trust me on this; you will never be happy if you aren't genuine in what you want in a partner.  As a good friend of mine once told me; "be you."  If you aren't good enough for a woman, it's her loss.

You don't want to be in a relationship where you change who you are to make someone else happy.  Sure, compromise will happen, but don't lose yourself to land a beauty.  You'll be miserable in the end.

24. Just relax!

When I first tried online dating, I would overthink things.  I would continuously redo my dating profile, message a woman and continually look if she read it, and constantly hit "refresh" to see any new messages to name a few.

When crafting messages, I would mull over the ideal approach.  Be it brainstorming the perfect opening line, how to respond to a message, or asking a woman out.  I suffered from analysis paralysis, afraid of doing the wrong thing, and taking an eternity to write messages.

Those days are long gone.  I don't sweat it.  If a woman responds, that's great.  If not, no biggie.  When I ask a woman out, I have a plan and get her number.  

Don't overthink it.  Just do. What's the worst that can happen?  A woman doesn't respond?  Big deal.  It's not the end of the world.  You will find a woman who you connect with eventually.

25. It's worth it!

I've had great relationships, started friendships, bad relationships, fun, heartache, stress, drama, pleasure, etc.  You name it; I've experienced it. 

I've had the ups and downs and the highs and lows.  Online dating introduced me to a wider net of women I would never run into on the street or anywhere else.

I wouldn't change anything; no regrets whatsoever because online dating is great.  I've made my share of mistakes and have had many failures, yet I've learned from them; yep, online dating helped me grow.

One of the best lessons learned about online dating is it's well worth it when you connect with the right woman.  

What are your lessons learned about online dating?  Comment below!