Hi, Doc,

I’m a chronically single bisexual dude. I spent my 20s pursuing my passions, and I honestly wasn’t thinking about dating! Then I hit 30 and started to worry I’d missed the opportunity to find someone. I decided it was time to put effort into trying to date since it clearly wasn’t happening on its own, but I wasn’t in a good place mentally to start. It took a year of working on myself after that to get to a place where I finally feel confident and capable enough to actually put myself out there.

I’m on basically every big dating app and site now. I write thoughtful messages, pick people based on their personalities or interests, avoid conventionally attractive people since they’re already overwhelmed with interest, and I try to be open-minded about appearance, body type, age, gender, and sexuality. I put a lot of time and effort into making the best profile I can, and I try to connect with as many potential matches as possible.

I’ve kind of bombed horribly on all fronts. I mentally prepared myself for all kinds of rejection, but I can’t even get to the part where someone might reject me because I never hear back from anyone. I don’t really get any responses or messages or interest from women or men (not counting the random 50-year-old guys who just happen to be throwing out dick pics in all directions and seeing what sticks)

I turned to the internet to see what advice was out there for single people who had been unsuccessful, and it all seemed to boil down to advice for improving yourself, but… What if I’m already trying my best with all of that? To cover some of the “you have to fix yourself first” advice: I love fashion and dress well, I use an embarrassing number of skincare products and put a lot of care into my appearance, I’m at a healthy weight, in decent shape and work out a lot, and I’m already in therapy to work on my depression and mindset. I’ve met all the singles I could hope to meet through my current social circle. I already go to meetup groups and things like that. I’ve taken all the advice I can on taking good photos and having a good profile and sending good messages on dating sites. I have lots of hobbies (solo and with other people), hard-earned skills and interesting life experiences, and I think that I’m a good conversationalist, funny, passionate, caring, and overall a great guy with lots to offer! And it’s taken me a lot of hard work to reach the point where I can say that and feel like I’m good enough for someone else.

I honestly think I’m being the best version of myself I can, but the end result is that I’m still not good enough for anyone. There’s a big part of me wondering if I’m already following what all the advice says and doing my best but still failing, there must be something really wrong with me. I do have an ugly face and I’m short, but obviously I can’t do anything to change that, so I’ve been trying to make up for it with the good qualities that I do have. Lately, though, I’ve started to question if these might be flaws that other people won’t be willing to look past no matter how hard I try.

Nobody owes me anything, of course, and I don’t blame anyone for my lack of success, but it still stings to feel like I’m not up to par for anyone out there even at my best.

What do I do? If my best isn’t good enough, and my worst qualities are ones I can’t physically change, where do I go from here? When I started trying online dating a few months ago, I didn’t expect it to be a huge success, but I was hopeful that I’d at least be able to find a few people willing to go on a date with me. Now I’m starting to doubt I have any value to other people, and I’m very ashamed of myself, especially when I have single friends of all kinds succeeding with OLD where I’m failing miserably.

I’m doing my best to stay positive and barrel on, but I feel like all of my hard work to feel worthwhile has unfortunately started to fall apart as a result of this. Should I just wait to turn 50 and send out dick pics to all the strangers I can find? (joking!) Please help!

Doing My Best, Starting To Stress

First of all DMBSTS: you need to give yourself some credit for the work you’ve done. You’ve put a lot of effort into your mental health and into your life and that’s incredible. You have done a lot for yourself and regardless of how things are going at this minute, you’ve achieved more than you realize. You should be proud of all of that.

Second of all: You know what words leapt out at me here? “Dealing with my depression”. This is important. This is a significant issue and one that casts doubt on some of your claims of flaws because depression is a fucking liar. Depression whispers in your ear that your worst fears and anxieties are true, that all of your flaws are worse than you’d thought and that everything is pointless. And it is all the more convincing because not only does it hit your greatest anxieties, but it does all of this with your own voice. And I’ve been there, I’ve done that, I’ve done the work and I’m here from the future to tell you this fundamental truth: all of the things depression tells you is bullshit.  Such as, say, your supposedly “ugly” face.

As I’ve said more times than I can count in this column if I had a nickel for every self-proclaimed “ugly” guy who turned out to be anywhere between average to “no, you’re actually good looking”, I’d be having mecha fights with Elon Musk in a life-size mock-up of Tokyo 3. We already zoom in on what we assume are our imperfections when we look in the mirror, because we are hyper-focused on them. We see them clear as day and twice as large because we’re so familiar with the topology and landscape of our face that they stand out to us like mountains. But what we think of immense and of vast importance are often so minor to other people that they’d never notice unless we specifically drew their attention to it.

Depression and anxiety take all of that and dial it up to 11, and then it snaps the dial off because FUCK YOU THAT’S WHY.

Like I said: depression is a liar, and it will beat you down if you let it. But recognizing it and learning how to fight it makes all the difference. That’s why it’s good that you’re working with a therapist about this.  Getting depression under control and realizing just how much of it is bullshit is going to be the single best thing you can do for yourself. Learning to love yourself is a huge part of relationships. It’s not that you have to think you’re the hottest thing since World War III or that you’re perfect and that anyone would be a fool to NOT be with you. It’s learning to believe that, even if you’re not perfect, you’re still worthy of love. Even if you have flaws, you’re still worthy. Even if you’re not having the success you wish you had, you’re still worthy.

That’s something to hold on to, even when it feels like there’s nothing you can do.

But that doesn’t mean the answer is “stop trying to date until you get your depression managed”; it’s just tact that you should pursue while pursuing dating. Another is changing up how you’re approaching dating because right now, you’re getting in your own way.

So let’s talk a little about what you’re doing and what you can do differently.

I think the first problem is that you’re trying to do too much all at once and you’re giving yourself a nasty case of burn-out. This is really common, especially among guys. There’s a tendency for men to be what The Love Gap author Jenna Birch calls “linear developers”: we tend to treat everything as a linear process. To get to X (in this case, being “ready” to date), we have to have get A1 – W28 done first. Once all that is taken care of then we can date. And that means that we spend a lot of time doing anything but dating, so by the time we’re ready, that’s the only thing we do. So now we’re insanely invested in the outcome because we’ve just put all this work into getting to this point for years.

And it makes things difficult because a lot of times, the people we want to date – particularly straight women – develop like a web: cultivating and developing their lives more or less simultaneously. So they’ve been ready to date and frustrated by the fact that they’re on a different timeline than the people they’re interested in.

So now there’s a massive disconnect between potential matches, which fuels the frustration because here we are, we’re finally ready and nothing is happening. And that kicks us square in the ghoulies because after living for this moment, our self-worth gets so wrapped up in the outcome that this lack of success means that everything else we’ve done is worth less and we’re worthless.

And our emotional resilience falls apart.

Take in your case, DMBSTS: you’re putting in all the effort and getting nothing back, which is cratering your self-esteem. Part of the problem is that, frankly, you’re putting in all the effort. You’re throwing so much of yourself into this that you don’t really have any reserves. Worse, you’re doing it so broadly and inefficiently that you’ve made it hard to get any returns on your emotional investment. So you need to dial this back.

The fact that you’re on “every dating app out there” is an example of this. Even allowing for hyperbole, when you divide your attention over multiple dating apps, you end up spreading yourself too thin. You have too many people, too many apps, too many messages and spend too much time on all of them. You end up with the paradox of choice (too many options) and diffusing your time and energy. So start by narrowing your focus to one, maybe two apps at the most. Different apps have different cultures and attract different audiences. Match is more oriented for serial monogamists while Tinder is shallow and superficial by design. Bumble and Hinge are both aimed more for people looking for relationships, while Scruff, Grinder and Recon are far more hook-up oriented. OKCupid, the 400lb gorilla in all of this, tends to be more raucous and “anything goes” which is both a blessing (everything under one roof!) and a curse (people looking for one-night stands keep deluging people who’re looking for commitment).

Pick one or two that most match with your immediate goals and the type of person you’re looking for, and let your other accounts go inactive for a while. If you decide to switch apps, take a one-in, one-out approach, to keep yourself from getting overwhelmed.

Next: dial back the level of investment you’re making. As counter-intuitive as it may seem – even considering some of my advice on the subject – you are putting too much effort into that first message. It’s good to be personal and thoughtful, but there comes a point where you’ve invested so much in that message that the lack of response wrecks you. Your goal should be two-fold: get them to check out your profile and get a conversation started. That’s it. Don’t overthink it, don’t put too much time into it and don’t write them a novel. Give them a reason to check you out and to reply to you. Ask a question, have plenty of conversational hooks in your profile and then move on to the next person.

Just as importantly: message the people you’re attracted to. That bit about not messaging the conventionally attractive folks? That’s not you making a smart play, that’s you screwing yourself over because you don’t believe they could be interested in you. It’s just another way that you let your depression rule your life and cheat yourself out of potential happiness. They may be getting tons of messages but that doesn’t mean that you don’t stand a chance. Not messaging them doesn’t improve your odds, it just means that you continue telling yourself that you’re not good enough to try to even talk to them. Reinforcing your own sense of worthlessness isn’t a successful dating strategy, even if you’re dressing it up in a misplaced sense of consideration for others.

The third thing to keep in mind: online dating should be a supplement to how you meet people, not a replacement. Even in this day and age, most people aren’t meeting their partners via Tinder and OKCupid, they’re meeting them through work, through friends and through shared activities. Living your life in such a way that it brings you in contact with other people with similar interests is part of how we increase our potential dating pool. And in fairness: you’re doing that. But part of the problem, I suspect, is that you’re approaching this as “If I go to X, I will find Y people I want to date,” which is a mistake. Your goal in meeting people should be just that: meeting people. If some of them are folks you’ll want to date right off the bat, then yahtzee! But most folks aren’t; that’s nothing to do with you or them, that’s just numbers. We’re not attracted to everyone we meet, or even the majority of people we meet – especially right off the bat. The number of people we meet that we want to date right away is small. The number of people we grow attracted to as we get to know them? That’s much higher.

Just as importantly, you may not meet people you want to date at that Meetup or in your social circle… but you more likely to meet someone who’ll introduce you to the people who you want to date.

That, however, is another place where you have to be willing to take the initiative. If you’re looking to increase the number of potential partners, then ask your friends for help. Let them know you’re looking to date and do they know anyone that you might click with? They may not have anyone in mind right off the bat… but the window doesn’t slam shut if they don’t have anyone right then and there. You’re meeting and getting to know folks all the time and so are they. So if they know you’re single and looking and they meet someone new who might be your particular shot of whiskey? Then they know to try putting you two together.

But the most important thing you need to remember? Dating is a numbers game. You maximize your odds of meeting people as best you can, but there’s always going to be an element of chance. You need the right person in the right place, at the right time. That can be hard to get to line up. Some of the folks you meet may not be in the right place, for you or for them. Or they may not be the right person yet.

A wise man once said: it’s possible to make no mistakes and still lose. That’s not weakness. That’s not a sign that there’s something wrong with you. That’s just life. But as long as there’s life, there’s the chance to make it all work.

What you can’t do is compare your journey to anyone else’s. Some people have an easier time in dating and that has everything to do with them and nothing to do with you. If you were to do the exact same things they did, you would get entirely different results than them. Not because there’s something wrong with you, but because you’re not them. You’re on your own journey, carving your own path in ways that are unique to you.

And your journey is far from over. This isn’t the end. This isn’t even the beginning of the end. This is the end of the beginning.

Good luck.