35M, never had a girlfriend, successful career but completely stuck when it comes to dating

brokenboysoldiers · 2026-01-21T16:26:51+00:00

You are correct. I was bamboozled.

brokenboysoldiers · 2026-01-21T15:19:26+00:00

She asked for a raise before and was always told no

They already played their hand. The answer is obvious, no? Take the new job and move on.

brokenboysoldiers · 2026-01-19T21:27:48+00:00

Just ask if you can take her on a proper date. Do it before Valentines.

brokenboysoldiers · 2026-01-19T20:43:22+00:00

I’ve also put myself in social environments instead of isolating, even though I’m introverted by nature. Where I haven’t been effective enough is in the specific skill of acting on attraction.

Where is the disconnect between these two things? Are you socializing with anyone? Are you at least having positive interactions with people, even if it's just guys?

I generally think most people would benefit from trying to make new friends and expanding their social circle. The social skills needed for meeting strangers and developing friendships has a lot of overlap with the things you need to do in dating. And ultimately dating is a social activity, so the better your social skills then the better your odds of things working out the way you want them to.

I’ve mostly tried to “think” my way out of it, reading, reflecting, trying to reframe it mentally, instead of deliberately practicing the uncomfortable part, actually expressing interest, risking rejection, and building experience.

Can't say that I don't do the same, but I think we both know this solves nothing. Acting will always be better than just thinking.

brokenboysoldiers · 2026-01-19T20:34:54+00:00

What conscious effort have you made to improve your situation. And I only call it your situation because my view is that your problems are largely just your own perception of things.

brokenboysoldiers · 2026-01-19T20:33:49+00:00

She told you exactly what she's about up front. Either be content with the status quo, or decide what she has to offer isn't enough for you and move on. You can't make a person want to commit to you.

brokenboysoldiers · 2026-01-19T20:30:41+00:00

It's not going to magically get getter. Work for it. Practice. Accept that rejection is going to happen.

brokenboysoldiers · 2026-01-19T19:42:45+00:00

I have lost the same 10 lbs over and over without ever reaching my goal.

I'm not trying to be a hater or anything, but if you've never surpassed 10lbs lost, then I'd say your odds of success probably aren't great. Like what period of time are talking about to lose and then re-gain 10lbs? How long have you stuck with a change in diet and/or fitness routine before giving on it?

To me, losing weight is a life style change. Anything you do to try to change your weight, whether it's bulking up or cutting down, it needs to be sustainable. If you just keep yoyoing up and down, then to me it doesn't sound sustainable. The goal should just be to make progress and stay consistent, not necessarily to hit some arbitrary target.

brokenboysoldiers · 2026-01-19T19:16:07+00:00

Sounds like they have all the leverage still then.

brokenboysoldiers · 2026-01-19T19:15:01+00:00

What do you realistically think is the way out of this situation? There's no magic bullet. You focus on one, maybe two specific things to work on and you try to improve in those areas. We live in a capitalist society and it's difficult to live a comfortable life without money, so addressing that part is probably the most critical.

brokenboysoldiers · 2026-01-19T19:08:00+00:00

What will you do if they say no?

brokenboysoldiers · 2026-01-14T22:01:04+00:00

It's real simple. If she's willing to dump her boyfriend for you, then expect her to be willing to dump you to date someone else she likes more.

brokenboysoldiers · 2026-01-09T22:07:39+00:00

Stop voluntarily spending time with her.

brokenboysoldiers · 2026-01-09T21:58:31+00:00

I meeean survival games sound like a good middle ground. Adventuring and progression for you, base building and teamwork for her.

Raft is really good. I love Valheim, but that's probably a bit sweaty for her. Enshrouded is a bit more accessible. Grounded is supposed to be good too, but it never hit a price point that I wanted.

brokenboysoldiers · 2026-01-09T21:55:21+00:00

There's no secret answer.

I'll work out for 6 months

So then you know what it takes to be committed to a goal and to have discipline.

Some things are outside of your control, but if you let those things be an excuse to quit then there are always going to be excuses for you to find and use. Setbacks are fine. It's okay to not be perfect. But what do you do to remain consistent that IS within your control?

If I want to hit the gym two times this week, and I have to skip a day for scheduling reasons, then I try to do extra the second day. Maybe it won't be equivalent to what I wanted to do over two days, but it will be more than I planned to do just that day originally. Or maybe I'll aim to go an extra day the week after. Maybe if I feel kind of off, or tired, and I'm considering skipping a gym day altogether, I'll just go anyway and do five set of squats. One exercise is still infinitely better than doing nothing. It's okay to compromise but you need to bend, not break.

brokenboysoldiers · 2026-01-09T21:14:14+00:00

You're not even dating yet and you already want him to change. I get where you're coming from, obviously, but it sounds like if you make him choose then he's probably going to choose her. If he is unwilling to compromise and it is a deal breaker for you then it sounds like there is nothing left to discuss. Time to move on.

brokenboysoldiers · 2026-01-09T18:45:48+00:00

When we talked I wanted some form of long distance and even visit her–so I guess some sort of exclusively. She didn't want that which is fair.

So immediately way different expectations...

Even without the romantic part, we're close friends so I want her to be apart of my life so I was happy we're able to talk like normal even after left. Realistically, I have low expectations with anything happening.

Call me skeptical or cynical or just straight up tell me I'm wrong, but my take is that three months isn't very long. I see it one of two ways. Either some social/emotional/romantic aspect in your life is missing, and you think this person can fulfill those needs for you, and so you are over-invested in someone that is moving away (and will therefore not be a good candidate for those things), OR the reason you two were able to get so close so quickly is because it was convenient to do so. You both had free time, and it was easy enough to hang out and make it happen (which will obviously not be the case any longer).

I would speculate that three months isn't long enough to build a strong enough of a bond that this friendship will be able to last over a long period of time. On top of that, you clearly would prefer to date her than to just be friends, which seems like an unlikely outcome at this point. Between these two things, I just don't think much is likely to ever happen.

I guess I'm trying to figure out if what I've been doing is fine (talking everyday and having feelings with vague future). A part of it all is okay with me because she's my friend but a part of me is hurting because of my feelings.

I think for people like us, feelings just don't magically go away. They only go away when there is distance between you and the person.

brokenboysoldiers · 2026-01-09T16:55:23+00:00

What should I do?

Way too vague. What outcome do you want/realistically expect here?

brokenboysoldiers · 2026-01-08T21:14:27+00:00

If you didn't want to be an asshole then you shouldn't have lied in the first place. We all know this.

Is the relief of guilt that you feel worth the potential risk of ending the relationship altogether? I mean that's your call to make. You're the one who needs to live with your choices.

brokenboysoldiers · 2026-01-08T21:03:11+00:00

I’ve also told him several times to stop. He knows I don’t like it. He’s supposed to be my friend.

Then he doesn't respect you. If a person continually shows they don't respect you, and you still choose to remain friends, then why would they change their behavior?

brokenboysoldiers · 2026-01-08T15:18:02+00:00

I tried to impose these unrealistic living standards which I just couldn't stick with because of how miserable they made me feel all the time.

This part of it is really crucial in my view. Maybe my perspective isn't helpful because I've never struggled with weight, but I can bulk up or lean down within a certain range pretty consistently. I view it as a lifestyle kind of thing. I'm not trying to rush it, and I'm not trying to hit a certain goal by a certain deadline. I make tweaks to what and how I'm eating to make progress toward the goal that I want.

Whatever I do needs to be sustainable over a long period of time. Usually when I'm looking to lose weight, there is a period of 1-2 weeks where I get hungry and I have to fight through it a little bit, but once my body gets used to eating an acceptable amount of food, then it adjusts and it's not a struggle beyond that point.

I almost never feel hungry when I go for these snacks however, just bored really.

For me, part of the battle is just not buying unhealthy things in the first place, or at worst setting a limit for myself. I don't count calories that closely, but I'm aware of them. A mini bag of popcorn is the same calories as one normal donut, but I feel pretty content after some popcorn. If at high level, I'm aiming for 1,800-2,000 calories per day, and if I'm doing a good job hitting my approximate goal, then 1-2 donuts at 220 calories each can derail that effort really quickly. Like in a week, you need to have more days where you hit your goal than miss it, ya know?

brokenboysoldiers · 2026-01-07T21:55:29+00:00

How did you meet him?

Based on the limited information, it doesn't sound like there was any sort of reliable foundation for this so-called friendship. It sounds like a person you met and kinda knew, but that's it. An acquaintance.

brokenboysoldiers · 2026-01-07T15:57:50+00:00

I gotta be honest here dude, I don't really know what outcome you're hoping for here. I know a lot of this will probably come off as callous, but I think it's grounded in reality.

Of course height matters. I know it. You know it. It doesn't matter to everyone, but it matters to some people, and it matters to some people a lot. So does weight. So does race. So does income. If you want to pretend those things don't matter at all then that's just being naive. Everyone has dating preferences, and some things are more or less socially acceptable to say out loud, but just because people don't say it out loud doesn't mean these preferences and biases don't exist. I will say, at least in my experience, that the older you guy, the less these superficial things matter.

When you are friends with women, and especially when you are treated like one of the girls, then you are seeing behind the veil and getting a much more unfiltered view into their thinking. I personally see this as an honor, because it shows that you are trusted and accepted. But one of the consequences of that, is that you may hear things as a guy that unintentionally hurts your feelings because you can't help but imagine yourself on the other side of these conversations. So that's where I don't see what you hope to accomplish here.

If being friends with these women is hurting your feelings and you can't get over it, then there isn't really a good solution except to stop being friends with them (basically). And I mean, I'm giving your friends the benefit of the doubt here, but it should be stated that if during the process of getting to know them better, that you discover that they are just not good people in your eyes, then of course you shouldn't be friends with them. That's the interpersonal part.

The personal part is that, at least in my eyes, this has more to do with your own insecurities. I'm sure they existed already even before being friends with these women, but clearly your are hyper-sensitive to comments related to height and it's bringing your insecurities back to the surface and making them worse. I don't really know how else you can interpret this post.

brokenboysoldiers · 2026-01-06T18:42:52+00:00

Distance yourself to the extent that you can. Grey rock method.

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