My dating life is really disappointing, am I doing something wrong?

Here’s The Thing is an advice column/newsletter where I mostly beg people to either stop dating someone or to ask their crush out. Or I talk about weird things that came to my mind that no one is paying me to write about. I can never decide if I should capitalize the “the” in Here’s The Thing or not; apologies on lack of consistency. 

You can submit your own question—or yell at me about how I’m wrong—by emailing me at

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I’m writing in about my disappointing dating life. It is virtually non-existent and I can’t help but continue to think it is something I’m doing wrong. I have no problem talking to women or forming friendships with them. I am confident in who I am as a person and others can tell that about me.

What I think my issue is in general is that I don’t really give off the vibe that I am a potential romantic option to the women around me. I don’t think it is a case of hiding from them. I work in the restaurant industry of New York City which is as full of dating opportunities as you can possibly imagine. I am open to any woman that I could cross paths with. But what happens more often than not, the women around me tend to vie for every other guy. I don’t want this to come off as angry at all by the way. I would never blame other women or people for that. I especially don’t want to come off anywhere at all near off incel territory.

So it must be something I’m doing. If I had to guess, I would say that it is because I don’t do enough to make myself be seen as a dating option. I think I get along with women and then I get complacent and things always just stay on a friends level. Which isn’t a bad thing. I have many female friends and I appreciate it. They’ve made me a better person and man. But there comes a point where this has happened so many times that I start doubting myself. 

The thought has crossed my mind that it could be a physical thing. I am shorter than the average male, 5 foot 5 inches. I am on the heavier side which is only exasperated by the short thing. I do take care of myself however, and exercise when I can. Plus with the physicality of being a server at a busy NYC restaurant, I’m always moving. So maybe it’s just the matter of women not finding me physically attractive immediately. Which is fair. We’re all visual beings. I’ve accepted that.

But there is another part of me that tells myself that it’s a dangerous slope to be on to think that I have to look a certain way or be a certain height or weight to deserve someone’s affection. Anything of that that I could change would take a long time, and I don’t think I deserve to be alone for that time just to achieve some abstract goal of happiness.

I said earlier that I don’t have problems talking to women, and I don’t really. Generally, I struggle starting conversations, but I definitely keep one going. But I think I hesitate to cross that line into saying something more intimate or “daring”. I might have gotten it into my head that women don’t want to be talked to in that way by someone like me. It makes me think of that line from the 40 Year Old Virgin where Steve Carell says, “I respect and love women so much that I completely stay away from them!” It could just be a fear of rejection and I’ve already answered all of this for myself. Maybe it just helped me to write this all down.

Maybe it’s just a bad luck thing. That I haven’t met the right person or something along those lines. But if there was something that I could do, I’d do it. Without sounding too cocky, I do consider myself a genuinely good person. A kind, generous, and loyal person. I know that I have a lot to offer and I hate the idea that I might be messing up chances to share that with somebody. Plus New York City can be a lonely place, and on nights like these that I stay up avoiding writing and overthinking things, having someone to talk to and sit with would be amazing.


If I had a dollar for every person who has written in to me asking why they aren’t dating someone, I would be able to buy these boots, which just so happen to be the only thing I have ever wanted in my entire life, other than when I wanted the American Girl Doll Josefina from 1998-20011. And your letter, my friend, seems to be in the top 10 percentile of letters when it comes to self-awareness. (I say “seems” because maybe you’re actually 6’9” and already dating a bunch of people currently and this letter is part of an elaborate delusion). If I assume you’re reporting on yourself fairly accurately, which it really does seem like you’re doing, then I believe you’re in a great spot.

Sure, it may not feel like you’re in a great spot, but I’ll put it this way: you have all the tools to get to where you want to be. If this were a road trip where you had to get from Cincinnati to Sarasota: you are in Cincinnati, you know you’re in Cincinnati, you’re in a car fully stocked with snacks and a working gps system, plenty of air in the tires and working AC and radio. If you were not so self aware, if you were not as confident about yourself, if you were worse at conversing then it might be more like being dropped in the middle of the country with no clues as to where you are, with a flat tire and no money and being told to go find Sarasota.

The absolute #1 Most Sick Fact About Dating is that you can be a total catch, you can do all the “right” and “healthy” things, you can be kind and generous, hardworking and open and still you will be single. If I were in charge, I promise this would not happen. I promise that people who were ready to date, who were lovely to others would not be single. Alas, I am not in charge and sadly, neither are you.

Dating/finding a partner is one of the most singular experiences in that it is the EXACT opposite of a meritocracy, not in that the least deserving people succeed, but in that there is absolutely NO CORRELATION between who gets dated and who is in a good spot to be dated. I have friends who have dated abusive assholes, I have conventionally hot friends who have been date-free for five years, I know people who are “putting themselves out there” all the time and never meet people, and I know people who seem to get hit on everytime they walk more than 14 steps outside of their house. I know people who are never single for long and I know people who can’t seem to get a date and let me tell you, there is very little delineation between the groups.

Of course being conventionally attractive helps—I’m the last person on earth who will ever pretend otherwise; I think that’s foolish. There are many very, very, unfair and cruel realities of who is deemed attractive. TONS of morally neutral things like height, weight, race, disability status, etc, have been judged to matter in terms of hotness to some people, and those standards were set usually via violent and evil means. For example, I am not going to pretend to you that your height will not matter to all women. It will matter to some, and that is fucked, fucked, fucked, fucked. I’m only using your height as an example because you mentioned it specifically, and not because I think it’s somehow the most important thing about you or why you’re not dating. There are all kinds of things like this that all of us have to different degrees—uncontrollable factors that (and again, this is FUCKED!!! AND WRONG!!!) make us less appealing to certain swaths of people. This is just how it is. Not everyone is going to find us attractive or dateable. The same is certainly true for personality as well, but of course getting to know someone takes a little more time than just finding someone hot.

That said, you could not possibly more correct when you call the idea that you must look a certain way in order to date, “dangerous.” It is. Because even if some people aren’t into you, other people most certainly ARE. I guarantee. Getting caught up in what it is about you physically that might turn some people off is not a great use of time. That time could be spent making cinnamon rolls from scratch or going on a weekend trip or jerking off.

The simple shit-ass fact is that finding someone who is attracted to you at the same time you’re attracted to them takes time. Dating is not, despite people espousing this constantly, a numbers game. It’s a waiting game. What you do with that time is up to you, but you cannot hurry up the timeline of meeting someone you really like who likes you back. At least, I’ve never heard of a way of expediting the timeline. (If you’re looking to just hookup with people, then sure, Numbers Game your way through Tinder, but for an actual connection, there’s no way to hurry up and meet a person who excites you, whom you excite when you’re both ready to date).

I do absolutely think that it’s worth being slightly more flirty with people you’re interested in. Flirtation doesn’t have to cross lines. In fact, it shouldn’t! You can give a person clues that you’re into them without saying “I want to take you home and fuck you sideways,” (too much). Ask people you’re interested in out! EVEN FRIENDS! A lot of people who are dating now started as friends. It’s a very classic way to meet people. I don’t think expressing possible romantic interest should, in an ideal world, harm a friendship, especially if you express that in a casual way. The best advice I have for friends-to-asking-someone-out moves, is to be very casual, be open to hearing “No,” take the first sign of hesitation as a “No,” and take every “No” as final. (That doesn’t mean end the friendship, just don’t wait 5 months and ask again or something).

When you ask someone out (friend or otherwise) it can—and probably should—be in a lowkey way. “Hey, do you want to get drinks/coffee/lunch with me sometime?” is very low pressure. I will also share with you The Chillest Possible Hangout Invite to ease yourself into being more clearly romantically available. It requires at least one other friend, but it works fairly consistently. Here’s what you do: with your friend decide to go to A Thing. That can be a bar, an event, a bier garten, a park, it doesn’t matter (well, make it covid safe). Then use this phrase to invite a hottie-whom-you’re-friends-with-that-you-might-want-to-smooch along, “Hey, Jimmy and I are going to X tomorrow night, you should come!” It suggests that you are already going to do that thing, you have someone else to go with you, it’s very low pressure, but that you’d like for them to come along. Easy, breezy, beautiful, DatingGirl.

Of course, as you know, no amount of flirting or making yourself more clearly available romantically guarantees that a person will be into you. You will, like the rest of us, have people who turn you down or who aren’t interested. Rejection sucks always! All forms of rejection suck! The best you can do is not let rejection change you or change how you treat people. Be sad about it, take feedback if you think there is something you can learn, be kind and move forward when you’re ready.

You will also have people that you’re not that into, even if you initially thought you might be. Again, it’s slow going to date people. It’s slow, slow, slow until all of a sudden it isn’t. What you do with the time waiting matters. It’s utterly fantastic that you seem to not be creating a narrative of bitterness for yourself and that you’re actively working to avoid dating wose creating self-esteem issues. The job of believing that you are in no way the reason that finding someone is taking a long time is DIFFICULT. Most people—likely you included—have moments of doubt. (It must be me. There must be something about me that is off putting or shitty. Surely I have to fix myself somehow). And I do think you’ve identified great things to work on—making it more clear that you’re interested in people, being a little more flirtatious, working on fear of rejection, etc. But also, you are already doing really well, even if it doesn’t feel like it.

In the meantime, if you get frustrated, angry, jealous, bitter, lonely, etc, please remember that all of those feelings are incredibly normal and fair. Please don’t beat yourself up about feeling down about this. It’s ok to be impatient. It’s ok to start a journal of complaints about the universe and write down each and every time you don’t get what you want. Just try your best to not live in those feelings, to not invite them into your head and let them take over your whole outlook on life. Try to acknowledge them and respond to them in healthy ways.

I’m so sorry it’s slow, I’m sorry to everyone for whom the process of finding someone is taking longer than they would like. It’s a very real pain, and thousands and thousands—millions, in fact!—of people have felt it and are feeling it. In the meantime, you’re doing amazing.

You can submit your own question—or yell at me about how I’m wrong—by emailing me at


I have also wanted just about every single object and baby animal and adult animal I have ever laid eyes on, but that is distinctly NOT the point.