"There's only one sin, and that's failing to believe you have a choice." -Jean-Paul Sartre
Question #92261 posted on 06/07/2019 10:06 a.m.

Dear 100 Hour Board,

I'm just so stuck with dating right now. Over the past 2 or 3 years there have only been 3 or 4 girls that I've really been interested in, and I did my part in each situation, but nothing really came of it. And I've gone on a lot of other dates during that time as well, but in the end I just wasn't interested enough.

On one hand I recognize that I'm probably being picky, but on the other hand I can't make myself be interested in someone (as much as I genuinely wish I could and have kind of tried before). And I know there's the argument for giving someone a chance (and I think I generally do) and you don't have to be in love with them to date them... but I should at least be excited by the idea of dating them, right? They deserve someone who's excited to date them. I briefly dated someone that I kind of liked who really liked me, and it was a good experience, but eventually I broke up with her which sucked for both of us. And break ups are just a part of dating, I get it, but I really want to at least be excited about dating someone rather than just kind of interested, you know? Otherwise it feels dishonest and not than fun for me anyway.

On top of all that, it's so discouraging to be consistently rejected by the people I do have genuine interest in. There's one girl right now that I'm interested in, but so far it seems more likely that she's not interested than that she is. And I should try to do my part anyway just in case, but she's really busy and it makes it that much harder to get to know her, and knowing that all my energy and effort is probably going to end in rejection anyway is really discouraging.

And maybe you're thinking that I just like "the chase," or just like girls that are "hard to get" or something. I've thought of that. And without explaining it in every little detail, I can say I'm pretty sure that's not the case.

So yeah. I don't know what to do. I'm discouraged by how dating has gone for me for the past... forever. And I would like to start going on more dates but the idea of going on dates with people I'm not interested in just for the sake of dates, or with people I like who statistically speaking are going to reject me, or with people that end up liking me that I then have to reject, is really discouraging as well.

Any advice, or stories, or really any thoughts about this at all would be appreciated. Thanks :)



Dear Tired,

I'm sorry that dating sucks right now. I can see why that's so frustrating. Sometimes dating just sucks. It's good to be hopeful and all, but sometimes I think it's also okay to vent and realize that dating sucks. Hopefully writting out this question has helped you feel a little better. If you ever want to talk more about it the 100 Hour Board is always down to listen so feel free to email us okay?

Why does dating suck? I think one of the frustrating thing about dating is the total randomness of it. When you're working on homework you know how much you have left to do and there's often answers you can check in the back of the book. In dating it's totally random. Like, you might be going on plenty of dates but then suddenly nothing happens for a few months. You might be in a relationship that's working and then it suddenly ends. You have no idea what's gonna happen next. You don't know who you'll meet, or how dates will turn out, and all that uncertainty can be frustrating.

But to me that's also the hopeful and super encouraging part of dating. Even if your entire dating life up until now has sucked or has been nonexistent all together, next week you could meet the one and things could just click and turn into a fairy tale ending. Great things are yet to come no matter how unlikely that might feel right now. Try not to be discouraged if the random hot mess that is dating hasn't worked in your favor yet, because sometimes that's just how the randomness goes. When your turn comes it will be unexpected and magical and wonderful.

I've got a great example for you. About a year ago one of my friends just went through a difficult breakup. Over the past few years they had gone through tons of relationships and all of them had ended badly. It seemed like they were trapped in a loop of relationships that didnt last. There was this other person who never really had much of dating life. They had never been in a relationship and not really gone on many dates. It seemed like dating wasn't going all too well for them either.

But then they met each other and started dating. The years of dating fails disappeared and everything was super natural and right. They got engaged and eventually were married! They are an awesome couple and now it's hard to imagine them without each other. The crazy thing though is that just a year ago no one could have expected it. Things weren‘t working and then suddenly they did and it turned out awesome.

The best thing about dating is that it only has to not suck once. You really only need one relationship to work out. It's frustrating dealing with all the in between but once the right person comes along you get to enjoy it AND you get to be done with dating forever so that's nice too.

Hopefully you found this encouraging. Dating can suck sometimes but that's okay. You totally got this and I’m sure that you'll find an awesome relationship! I just can't tell you when cause of the darn random nature of dating. So uh.. keep calm and carry on!




Dear Tired,

I'm going to try to not be the married person who gives dating advice like it's all easy, but I'm married and I'm about to give you dating advice. So... yeah, take this with a grain of salt.

1) I wouldn't get too bent out of shape that you're breaking up with girls when you find out you're not interested. If you date N people, you will break up with N-1 of them (or so). Most romantic relationships fail. Maybe that's a cynical way of looking at it, but it's also kind of freeing. If you're dating someone and you're not that interested, that's fine! That's most relationships! Being honest with that person about your feelings and moving on is perfectly acceptable.

2) To your other point about dating for the sake of dating: that's right where I was when I met my wife. I was dating this girl who didn't even know who I was. She kept calling me Mark (not my name, Board Question #77014). Once, after our first date (where she called me Mark) but before our second date (called me Mark), she invited me over because she was studying for the GRE and wanted help. I threw on my jacket, rushed to her place, and ... SPENT THE EVENING HELPING HER STUDY AFTER WHICH SHE SHOWED ME OUT. <deep breath> I mean, seriously. But, I didn't stop asking her out "because," I said to myself, "I don't hate her and I may as well be going on dates." It was a sad time. Then I met my wife. All of a sudden, dating was natural. We spent time together because we wanted to. We sought out times to be together instead of fitting them into our schedules. We fell in love and got married. The end.

I'm not going to say that it will happen that way for you, but there are worse things than having your line in the water. You get to meet people, find out what you like (and what you hate), and have (mostly) good experiences (and, if not, good stories to tell). I know it sucks, but from reading your question, I don't think you're doing anything wrong either. Not sure if that's comforting or not, but there it is.


The Man with a Mustache


Dear tired,

It's Pride Month, which means you're legally obligated to only date men for the month of June. Sorry, buddy, I don't make the rules. Hope that helps your odds.



Dear you,

Well, I almost gave up hope after reading your question. I think you're dwelling too much on the past. Obviously you have to look at the past, but I think instead of just observing the past, you're dwelling there. You've set up a tent and started roasting a smore. You better not burn your marshmallow (unless that's how you like it, but that's a different problem).

Anyways, all it takes is one girl. I didn't have much success in the dating world, but I found the love of my life and now I don't care how my previous dating was. Maybe it will be the next one, or the one after that, or the one after that, or the one after that, or the one after that, or the one after that, or the one after that, or the one after that, or the one after that. But I think you'll eventually be successful.

Here's to trying until it works!

-Sunday Night Banter (motivational extraordinaire)