Why Online Dating Might Not Be For You

Comments 33


Maybe I was just doing it wrong. Totally possible. I’m good at several things, but there’s no reason to believe online dating is one of them.

I tried it pretty soon after my wife left. It was a very bad idea.

The first girl I met from Match.com liked me for real and actually got a little upset when she realized during our date that I wasn’t emotionally available. She politely explained to me how thoughtless and unfair that was. She was right.

The second girl I met ended up being the sister of a guy I happen to work with and we figured it out while chatting in an Irish pub. Bad idea!, we agreed.

The third girl was a very attractive hearing-specialist medical doctor who had just moved back to her Ohio hometown from Chicago. And even though she was a pretty doctor, she was the least-interesting conversationalist I’d ever met. Worse still? When the waitress at the Mexican restaurant asked us how we wanted our tableside guacamole made, I let her decide, and she chose to DOUBLE the amount of jalapeño, onion and garlic from how much they normally use. There wasn’t enough tequila in the restaurant to help me forgive that offense.

So, even when girls “liked” me online, meeting them was always mehhhhhhhhhhhhhhh.

But mostly girls didn’t “like” me.

Which is okay. I’m certainly not for everyone. However, as time marched on, and I heard others’ experiences, and I watched from the front row as one of my best friends navigated the online-dating landscape at the same time, dealing with many of the same things, I found myself souring on the process.

‘You Seem Like You’d Be Really Good at It’

The girl who cuts my hair asks about my dating life every time I see her. She likes to know who I’m talking to and whether there’s girlfriend potential.

A couple days ago, she asked “Are you online dating?”

I said no.

She asked why.

I said it’s not a good idea for guys like me.

She said: “What!? You seem like you’d be really good at it!”

Married women always think I’m swell.

“There are certain kinds of dudes who I imagine have a great time dating online,” I said. “You’ll just have to take my word for it that 36-year-old single fathers who look like me aren’t among them.”

“You’re an attractive guy. Plenty of single women would want to date you.”

“Thank you, but it doesn’t work that way on the internet.”

“I’ve been married a while and have never dated online. What do you mean?”

Glad you asked.

The Internet vs. Real Life

I’m not hideous to look at. My self-awareness extends to my self-perception. I’ll never be mistaken for a dashing billionaire playboy or movie star, but history suggests the general female population finds me more attractive than my spotty-at-best dating life might indicate.

And here’s why:

The experience of standing in front of someone and talking to them and watching them move around and interact with you and others is, historically, how people decide to whom they are attracted.

And I do pretty well with that.

People don’t often think of it this way, but sexual attraction (from a purely physical standpoint) is a simple pass-or-fail test. We either find a person attractive enough to get naked with, or we don’t. One or the other.

What determines whether we actually get naked with that person are the 90% of things that actually matter to us. How they make us feel. How they treat us and others. How their personalities mesh with ours. Whether we enjoy talking to them and want to do more of it. Whether we discover common interests and build intimacy. Whether they are safe and trustworthy, however we define that.

That’s how people become attracted to one another.

I’m decent-looking enough to pass the pass-or-fail attractiveness test most of the time, and I’m smart and friendly and kind enough, and occasionally charming and engaging and funny enough, that the person I’m standing in front of will sometimes want more.

But, if your Dating Résumé is like your Employment one, I have a few things working against me.

I’m 5’9”. Women tend to prefer tall men. But since the average female height in the United States is 5’5”, and the vast majority of women I meet are shorter than me, it tends to not be much of an issue in-person.

I’m graying. I have no idea how that plays in the minds of women either online or in-person, but my best guess is that it makes me more attractive to older women than it does to anyone my age or younger. I won’t pretend to know.

I’m divorced. To someone who has never been married, it means I come with baggage. And to divorced women who got screwed over by their exes, it could trigger feelings in them that maybe I’m like their ex-husband.

I’m a father. I have a 7-year-old son. Single women with no children aren’t always keen on becoming a stepmother to a child they’ve never met, or competing with that child’s mother. I imagine childless women frequently rule out fathers because of that. Single mothers are more likely to appreciate what a father brings to the table, but depending on her individual circumstances and experiences, may also be unwilling to take on a parenting role to another child.

When you meet someone in person, these things are often overlooked. After all, my son is never with me in adult social settings, and dating activities only occur when he isn’t home. Should the relationship ever graduate to “love,” I imagine parental status would be something of a non-issue.

But the Internet, Though…

Imagine being a single woman establishing your preference filters on an online-dating site.

As soon as you make your profile live, you have virtually unlimited options because of all the men vying for your attention. Whether you’re on Match or OKCupid or Tinder or FarmersOnly.com, you flip it on, and the requests start pouring in.

When you have your choice of anyone you want, are you really going to pay attention to divorced 36-year-old gray-haired guys with kids, when you’re 31, never married, no kids, and prefer tall men? When that’s all you know about them?

Of course not. I can’t say I blame them.

If you’re a divorced, single mother also attracted to tall men, are you going to? Possibly at a slightly higher rate, but single moms get plenty of interest online, too. It’s something of a numbers game, and even when they filter down to their favorite preferences, they STILL have virtually unlimited requests for their attention.

I’m a digital marketing strategist who is pretty good at understanding data and percentages. Shy, lonely guys with so-so social lives due to circumstances somewhat outside their control? It’s easy for them to want to sit safely in their homes and scroll through online-dating profiles where they don’t have to make eye contact and try to say something smart and attractive to a pretty stranger in public while simultaneously shitting themselves.

I get it.

But I’ve grown to believe there are a lot of people who probably shouldn’t subject themselves to this losing formula.

And nearly three years ago, I was one of them.

Broken and empty. I was desperate to fill the void. Desperate to feel liked by someone again. Desperate to feel wanted by someone again.

I turned to the computer screen because it was easy and low-risk. Just as millions of others do.

Be Brave

You know which camp you fall in.

You’re either someone who dates online because it’s fun and works for you, or you’re someone who ATTEMPTS to date online because it’s a low barrier to entry and feels safer than trying to do it the old-fashioned and scary way.

I wouldn’t waste ONE SECOND of my life on a woman who would choose her life-long partner based on height, or who would view my beautiful son as some kind of annoying handicap.

Do you know how many dipshit moron 6’2” assholes with lots of tattoos and no kids there are? Good luck, sweetheart! Hope you like Hot Pockets and pro wrestling! (Point of clarification: There are brilliant 6’2” tattooed guys with no kids that I’m sure are really awesome and infinitely smarter than I’ll ever be. And even if they like Hot Pockets and pro wrestling, it doesn’t make me better than them. Probably.)

So I hope people out there—particularly the guys in situations like I was—aren’t losing sleep over people with personal values so different from their own. (Hint: It was never going to be Happily Ever After. So look forward to meeting the person with whom you can achieve that.)

It’s a funny little thing, but in my experience, there is no place with more pretty girls walking around by themselves than the grocery store. It’s uncanny, really.

Sometimes they have kids. Sometimes they’re wearing rings. And many times, even without those things, you can be sure there’s a boyfriend waiting for them somewhere.

And even though I don’t often do it, because it’s the scariest shit ever, I really want to encourage guys to be brave enough to say hi to these women when they want to.

With confident eye contact, even if you have to fake the bravery.

The next time I see a woman respond to a guy brave enough to say hi to her with cold-shoulder bitchiness meant to shame him will be the first time. And EVEN IF that were to happen, I think it’s safe to assume you two didn’t have a bright future anyway. Because she sucks big-time.

Keep grinding away at the computer, if you must. I do know people who have met wonderful partners that way.

But don’t forget there’s a real world, too, and in it you’re worth much more than strangers on the internet might suggest.

Make bold moves with people you see and want to meet.

Because the worst-possible result is simply more of what’s already happening.


33 thoughts on “Why Online Dating Might Not Be For You”

  1. I’m going through the this experience right now, very new to the online thing. So far, it’s horrifying. I like to meet organically! This was a great read, thank you!

    1. It’s been a solid two and a half years since I ventured down that path.

      I’m not trying to denigrate it, because I really do understand how helpful it is to be able to find single people. When we’re young, we’re surrounded EXCLUSIVELY by single people our age.

      Post-divorce? With kids!? Shittttttttt.

      It’s like lightening striking JUST to actually be in the same place at the same time as a single person your age.

      Then, they have to like you.

      Then, it has to be logistically feasible geographically or with parenting schedules to see one another.

      And THEN, you have to deal with all of the same things every other couple deals with, with the 50% or more failure rate.

      Totally scary, miss. I get it.

      Something tells me you’ll be alright, though.

      Just like me.

      Thank you for reading and taking a minute to comment!

  2. completelyinthedark

    Wow was this post ever timely!

    Was out Wed night with two girlfriends (women friends that I’ve no intention of dating) and two other guys were there, but they left independently and I was left having last drinks with my two lovely lady friends. Talk got around to dating. One has a first date with a guy we mutually know and I’m happy she’s met him. The other has a posse of guys she dates depending on what she’s interested in doing. Bravo to her.

    But I’m too freaked out by what’s going on in my life right now: having to move, find a new job, A LOT of change needs to happen first. But I DO want to meet someone new, since it’s been too long since my last gf. I have a lot of factors against me just now, and they succeed at eating away at my self-esteem.

    In the past, a positive change in the weather (jobs, places to live, new friends) has nearly always brought me closer to someone new I end of dating.

    So, yeah. Online dating sucks. For the reasons you state.

    But totally concur with the grocery angle. MAN, the opptys I’ve passed up there! 😉


    1. I’m both glad AND sorry that you get it, Mike.

      It often seems like there’s a lot more working against you than for you, and very little of it is your fault or within your control.

      Totally blows.

      Always wishing you well, sir. Great to hear from you.

      1. completelyinthedark

        yeah, the “in control” thing is what seems to attract women to men, akin to confidence. All but one of my past girlfriends came along at a time when I had just started a new job or had some brimming success—it showed in everything I did, and I could see it reflected back to me and made me more confident in asking them out.

        The one I met when I was depressed, but funny enough, she was initially impressed because I met her at a function and called her at her office out of the blue to ask her out. So that first impression must’ve carried over now matter how I was really feeling.

        Of course, we were the shortest relationship I can recall, so there’s that. 🙂

  3. I’m in somewhat of an opposite situation…never married, no kids, own my own business, (not wealthy, but I do okay and have ample free time)..but like you, I lack the “height” characteristic and am average, at best, in the looks department. So, I really don’t think you being divorced and a Dad is a negative, most every woman in my age range is divorced and a Mom…if they’re not, their standards are VERY HIGH…higher than my offerings.

    I’ve met many women, and did online dating on and off for the past few years, and here’s what I’ve found:

    I meet the girl who wants to invite you over to her place IMMEDIATELY who I guess feels that’s all she has to offer, and thereby can’t manager relationships or probably her own life. I meet the divorcee with kids, who wants a relationship, but then realizes later that “she’s just not ready” i.e. she deserves a better prospect with more potential. I meet the ones that seem nice, we hit it off, but just aren’t attracted to me (those are the most painful).

    It’s frustrating as all get-out. To top it off, I live in a rural community, and I’m highly educated, so another strike is there is absolutely NO WAY a local is going to go for someone like me. They prefer 6’2″ guys who like Natty Light and NASCAR. That rules out supermarket availability. I have to venture about an hour away into a more metropolitan area to even come close to meeting someone whose interest might be piqued.

    So, I feel your pain in online dating, though, as it is a “rejection festival of suck” 😀 for most men, I’m afraid. I recently started dating one I met about a year ago, and I shunned her for a while because I just wasn’t “seeing” us together. I never forgot her, and it took me a while to get back on her radar, because she was obviously weary of me after our first attempt. She relented, and we’ve been having a good, slow relationship since.

    She is not perfect, is a divorced Mom, and has personal issues…but is also a professional, and intelligent…things that I like. I like her kids and her personality. She’s sweet but independent, she can manage her own life. So, point of this being, I think I was a slave to that old adage, “the grass is always greener,” but I’m glad I have another opportunity. That’s the problem with online dating for male AND female. There is so much inventory, and the selection is always changing, that all of us get addicted to window shopping. Tell me you haven’t noticed the people on those sites with profiles active for YEARS!!!!

    1. That was really interesting to read. Thank you very much for sharing all that.

      “Rejection festival of suck”!!! <—- Nailed it.

      We get so caught up in our own experiences, it's hard to see how people in differing situations might be equally frustrated, but under different circumstances.

      Sounds like that's what's going on here.

      Someday, something is just going to happen. Hopefully something good. For every single person.

      I'm still hanging out in that waiting room.

      It's unbearable right on the heels of divorce. But now? I know it's going to be okay. Not easy. Just okay.

      I can live with that.

      Thank you again for reading and contributing.

  4. I think you are swell! In fact- I’m convinced I love you and you are who I should be married-to! Okay, well, I definitely think you are swell for sure! ? I LOVE reading this blog, thank you for writing! Always good stuff!

    1. Thank you, Alice. Few things are better than someone liking you and the work you do.

      What I think you mean is that you want to be married to someone who lives and behaves according to some of the things you’ve read here and agree with.

      I’m not even sure I can do all the things I write about. It’s HARD to walk the walk all the time. Me understanding what to do is not the same as actually doing it. I won’t know ’til I know.

      I want to believe that every guy, when presented with all the facts, would want all of the same things I want. That he would aspire to all of the same things I aspire to.

      I can’t emphasize it enough: Guys. Don’t. Know.

      So much of this relationship stuff. We just don’t know.

      I hope you’ll meet someone who wants to figure it out with you. Who will make your life his top priority, and who you’ll want to do the same for.

      In the meantime, thank you for the compliments. Super-flattering.

  5. The supermarket thing? That explains a LOT.

    I’d rather go to a night club without my husband than the grocery store. Suddenly, it makes a lot more sense!

  6. Hey Matt,

    I haven’t ventured out into the online dating world, but I totally get the idea that online dating reduces people to a handful of criteria filters. But at the same time, I would think that it could potentially be positive as well.

    Assuming people are honest (bwa-ha-ha), knowing up front that someone doesn’t meet one of the criteria that are “deal breakers” for you could be a good thing.

    For example, I don’t smoke, never have, and never will. I think it’s a pretty nasty habit, and with all the health issues associated with it I would never consider dating someone who smokes. I’m sure there are some amazing people out there who smoke, that I would get along with very well. But for me, that’s a deal breaker.

    I think many people in the online dating world apply too many filters, and as a result give themselves a very narrow pool of people to meet. But that’s really not that different from real life, where people do the same. It’s only as they get older that they change their standards because a) they are getting desperate or b) they realize some of the things they initially felt were important actually aren’t.

    You comment on the dating options being reduced when you are a divorced dad in your late 30’s. I get that, but I think part of the reduced options come with simply being older.

    I’m in my early 40’s. At this age, most “single” people are either divorced with kids, or if they don’t have kids it’s been a conscious decision. Kid’s complicate things,there’s no way around that. But just as many women look at a guy with kids and think “no thanks”, many men do the same.

    Dating in your mid 30’s to mid 40’s I would guess there are often young kids in the picture, and both sides hopefully get that. I struggle with the idea that no woman out there will ever love my kids the way I do. But they are part of the package that is “me”. Many women have the same concerns I’m sure.

    I do think that women can be a lot more choosy than men, but talking to some women in our age demographic who are in the dating world, there are a lot of terrible options out there.

    I think the hardest thing as you get older is, where exactly would you even meet someone? My life revolves around my kids, my community, and a few personal activities such as mens league basketball. Not a lot of opportunity to actually meet someone if I wanted.

    So yeah, online dating has drawbacks, but I think it’s still probably a useful option to have.

  7. All of this. Seriously. I would get through to the end of a profile where the person sounded halfway interesting and had things in common with me just to read:

    In order to contact this member, you must be:
    Height-weight proportionate

    Now, keep in mind, I have nothing against major age differences but that is just how my life has turned out. I don’t seek older for the sake of just being older. and I wouldn’t rule out someone my age, just as I wouldn’t rule out someone for not being my height or being overweight.

    I hate to say I thnk women have it worse than men with this but I do. I think, for example with weight, men are considered teddy bears and we are just fat. Then again, I may be the wrong person to ask about that.

    Sure, there’s the in-person option, but I don’t get hit on and I am too shy in real life to make a first move.

    (Alright, so I did get hit on…once, a few months ago. I was in shock so yes, I gave the guy my number. Didn’t work out, but maybe it will happen again in another 20 years 😀 )

    OK, all that to really just say, I completely agree and when I tell people I am no longer trying to date I may now send them to this post.

  8. What an absolutely dynamite post! I dabbled in online briefly a while back but never felt it was right for me. I could never quite articulate why but you’ve done it perfectly in this post. Just like yourself, I’m more likeable in person than as a profile on a screen with data attached to me.

  9. Hey Matt.

    My experience is a bit different.

    Personally I’m in a post marriage stage of my life where I want to experience other people. For me online dating had been awesome, but then again I may fit the target demographic a bit better and I’m not actively searching for my soul mate (and I actively state that so as to not mislead people)

    For me it’s a time thing. Between my 50% custody of my two amazing kids, my real job, my side business, my blog and my countless hobbies… I rarely have time to meet people organically.

  10. I don’t know what it is about you and your uncanny timing for posts. No more than 15 minutes ago I re-activated a profile on an online dating site that I haven’t tried in over a year. And then I saw this post.

    I’m one of those who prefer the organic way of meeting people, but find myself in a position that rarely places me in situations where that is possible. I would LOVE IT if a guy would approach me in the grocery store or, more honestly, a bookstore. That would absolutely be a win in my book.

    Thanks for the timely post…AGAIN!

  11. I have a quick story to tell:
    My husband and I broke up for a few months a few years ago and I decide to check out the online dating scene. It lasted one night. Beyond the men that immediately messaged wanting to hook up (& I didn’t have a picture!), I found one of my husband’s friends on there. Obviously, I knew him in person, but his profile? Wow. I can say that, in person, he is awesome. He’s a goofball, but he works hard, maintains his life without too much craziness, and puts his family first. BUT, his profile was poop. It didn’t even sound like him. Obviously a staged selfie, boring profile, cliches galore! Much to his dismay, I felt it was my duty to tell him that he had to either change that mess or quit the online scene LOL I mean, honestly, I would have passed him up if I didn’t know him. But, in real life, he doesn’t lack for attention even if he does attract some crazy ones at times. But, alas, one night was all it took to end my online dating venture. But, you are soooo correct about the supermarket!

  12. Okay, I totally understand what you’re saying. I online dated for a long time. I met different men, and even dated a few. Years past before I decided to change my perspective of it all. I decided to look beyond “my type” and guess what? I met an amazing man.. and now we are madly in love. I had honestly and truthfully given up. And this happened out of no where. Don’t give up though. I know how crappy online dating can be. Trust, when you least expect it, it will happen. I struggled for years being depressed and severely anxious because of my previous relationship. Time heals everything. And finding someone to make you feel full of life again is is a blessing! I hope you finds yours soon as well! 🙂

  13. Matt, it isn’t all terrible. That being said, it can be horrifying. Try being 58, imperfect (I don’t fit societies standards for beauty), divorced and an entire host of other things.

    Most men think I might be needy, I am not. Others think I might want to see their penis in pictures, I don’t.

    Oddly, I have met a few men who are interesting and funny. No spark but friendships have developed. I appreciate them and they expand my brain, this is great.

    What I wish? People would tell the truth on their profiles. If you are 5’9″, great say so. If you have tats, great so do I. If you smoke and drink, hey wonderful why lie. My favorite? Why does every single man say they are Christian and serious about it, but they would sleep with someone on the first date?

    Oh my litany could go on and on.

  14. Great post. It is too soon for me to even contemplate dating again but when I do, I do not look forward to it. I hated dating the first time. I never thought I would be in a situation where I might have to consider it… again.

    I am borderline introverted and have a hard time investing myself in other people. Well that is not entirely true. I have a hard time investing myself in other people who are not the love of my life. I also would have a hard time investing myself in someone who does not understand that my 5 year old daughter is the greatest thing ever from the get go (she is).

    Someday I am sure I will cross this bridge once again. I hate the idea of it though. Online/offline dating when you are over 35 just seems… weird.

    1. While I’m exceedingly outgoing and enjoy meeting people, every single other point you made is something I identify with very strongly.

      It’s statistically hard JUST to meet a viable person to even try to date. (Especially when you’re a parent.)

      Then you have all of the regular pitfalls of humanity to deal with once you do find someone to even try it with.

      I wish I had some advice. I don’t. I’m horrible.

      Thank you for reading and taking a minute to write. I get it, sir. I get it very much.

  15. Matt, I’ve read your posts on this before. I think setting up clear boundaries (must live within the same town or 25 mile radius) is all reasonable.

    When someone signs up for one of these services, you must put in the qualities you want from a potential partner as well. Some people, when they fill out their forms, are not reasonable. You should always ask yourself this: “When I am filling out these forms, am I putting in information for my preferences or a deal breaker?” I think there is a distinction there. For instance, maybe a girl would think 5’8″ is fine, but I prefer 6′. They should put 5′ 8″.

    If 100K is a deal breaker, to me that says don’t let the door hit you on the ass on your way out. Girls are assholes and yes, some look for money. If income is an important preference, lower it to your “deal breaker” threshold. Or just leave it off!!

    I’ve done Match.com before – many years ago. You know, it wasn’t so bad. The first few dates, I was fresh out of a very committed relationship. I had no business being there on some of those dates. One guy had 2 great dates with me and I cried through the third. I can’t imagine. how he felt. So I took a 9-12 month break.

    I just had to be in the right place mentally. And you know what? If someone pulled a fast one on me (one guy showed up significantly overweight compared to his profile picture) then I called them on it. I told them nicely what I saw, that we could have a wonderful dinner together, but that I was very busy and I was looking to seriously date for now. This happened twice. First guy cussed me out; called me a bitch and a whore; and promptly stormed out. The second guy was actually very sweet and we had a lot in common

    I found my STBXH a few months later. Total we have been together 15 years, but separated. But in my eyes, Match.com didn’t doom my relationship! IT DIDN”T MAKE ME HAVE ONE EITHER (sorry, I don’t know how to do italics for emphasis – I’m not shouting, I promise).

    We had a decent run, but I choose to be happy. He gave me a beautiful and smart son. Worth it.

    But I learned nothing in life is forever. So maybe I should have gone for the guy over 6′, or the one with hair, or the doctor instead of the guy teaching communications 😉

    The heart wants what it wants, no matter where it finds the source of desire. Oh, I had a 3 conversation policy in place as well – if we didn’t have a date set up by the end of conversation #3, then I moved right along.

  16. “Do you know how many dipshit moron 6’2” assholes with lots of tattoos and no kids there are?”

    Yes, we do.
    And this is my new favorite blog.

  17. It is the Type of women out there today that really makes Online Dating really Suck Unfortunately.

  18. I have no idea how old this is, but where does an older single dad even meet women these days? Volunteering, dance classes, yoga–great if you’re 32 and hot. No so much for the short single old dad. I’ve got people telling me to approach more women in coffee shops. Good option if you like college girls barely out of high school who may or may not have you thrown out for being the old guy harassing kids. Networking events, galas, upscale bars. Sure, I have a couple of grand laying around to meet women who’ve priced themselves right out of reality. My guess is that high value men sweep up and the rest of us die out fairly quickly after 45-which explains a lot about how many non-committal men are left for women to complain about after that age.

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Matt Fray

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