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Want to sort out my dating life... where have I gone wrong (long)?

raiden

Space Monkey
space monkey
Joined
Oct 1, 2020
Messages
132
Hi all. My dating goal is to meet a woman with whom I can settle down and have a family. I'm a mid 30s guy and I want to meet a woman satisfying these things. Under 30 (most of the women I dated were this age and it felt like a good vibe, plus I want the best chance of good fertility), into health/wellness (because I am), not a heavy drinker and not too curvy. I have failed to do well with any woman like that for 5+ years. Could we see where I have gone wrong? Here are my stats. LRs below refer to first time lay reports.

Q3 2023:
Worked with a dating coach who did some cold approach with me in the park. He also gave me some date coaching. Didn't get any dates or results and I started to have the feeling that he didn't know much what he was doing or at least that he couldn't help a basket case like me. So I stopped working with him. I had a previous dating coach before that but it's probably too far in the past to worry about.

Q4 2023:
Total first dates: 9, all from online dating systems.
Total second dates: 3
Total third dates or beyond: 0.
Total LRs: 0.
Worst fail: Two good dates with a woman who really seemed into me and was quite similar to me personality wise. While I was trying to schedule the third date, she sent some message about how she is not over her past dating experiences and, although she likes me, she will, for that reason, end things with me.

2024:
Total first dates: 18, all from online dating systems.
Total second dates: 5 (1 carried over from previous year)
Total third dates or beyond: 0
Total LRs: 1
The LR was with a woman who left town a few months later, so that relationship was not going to last even if we had wanted it to.
Worst fails.
-Ran the same dinner date with two women who fit the criteria one week apart and got dumped by both.
-Between date 2 and date 3, pretty much the same thing as what happened in Q4 2023 happened. I scheduled our third date, had to reschedule because of a family thing and got dumped.
-Went on a first date with a woman who satisfied the criteria and thought that I blew it. To my surprise, she wanted to go on another date. But after that date, I was summarily put into the friends bracket.

2025 (so far):
Total first dates: 12. 10 of these were from online dating systems and 2 were from dating events.
Total second dates: 4
Total third dates or beyond: Up to 5 with same woman
Total LRs: 1
Total dating events attended: 5
This year I got into a mini relationship. But the woman wasn't quite right for me so it was doomed to end, and it did. Fortunately, there is no animosity. But at the end of it all, I'm still stuck where I was at the start. That was where my LR came from.
Worst fails
-Went on what I thought was a good first date and agreed on a second date. Then the woman bailed on the second date because of issues at work.
-Went on two dates with a marriage minded woman. After each date she sent me encouraging texts like suggesting that we should go out again and used callback humor, calling back to stuff we discussed on the date. The third date was scheduled and she seemed excited for it. A few days before it, she called the date and the whole thing off, giving a generic reason like saying that she didn't feel a good connection. I feel like I screwed up with my texting but actually this is a common theme over the past few years. I'm still recovering from this one, because I was really ready to get into a proper relationship and be done with this dating stuff.



So how can I fix and diagnose this? A few notes about me
-I have poor fundamentals and poor looks. For this reason, I seem to get better results from online dating systems than at the dating events. At dating events, a woman could take one look and decide no. On the online dating systems, I look smart or nerdy or ambitious etc. in my photos and this would make up for my looks.
-I have poor logistics. I am in a big city and all these women were from all over. My family live with me. The LRs have been at the woman's place or a hotel. It seems like one way to stop getting killed between the second date and the third is to push for an intimate date before that. So do I need to seed the hotel pull in the first date and then suggest it for the second date (add one to the date numbers if the first date is a brief informational date of 1 hour or less)?
-I have started going to dating events this year because I really want to get this area of my life sorted and be on the path to becoming a family man. But I really don't seem to be competitive at them. The feeling is that I can make my opener to a woman and in a minute or two she has to get going to the bathroom or to her friend or to the bar. When it happens so quickly it seems like a pure looks based rejection that I can't do anything about.
-I likely have mild autism. But I think that it doesn't affect me more socially, but more the way that I argue and plan my life. So I can't really blame it for my bad results.
-I worry that my criteria are too restrictive. For example, when I say 'not too curvy' have I eliminated like 40% of women off the bat?
-I worry that I am not doing enough. I had an aim of 20 dates per year but this seems insufficient. I'd like an opinion on what a good work rate is.
 

Skater

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
May 10, 2024
Messages
54
It seems like one way to stop getting killed between the second date and the third is to push for an intimate date before that.
Yes. I'd say you need to be fucking way faster.

So do I need to seed the hotel pull in the first date and then suggest it for the second date
No. Pull after first or second. Otherwise, write her off. Also get an apt bro. No more dates till then. You're 30-something dude, looking for marriage, and living with the folks? Wtf??

20 dates per year but this seems insufficient. I'd like an opinion on what a good work rate is.
20 dates a week. Kidding, but for a year is ridiculous. At least, at LEAST one a week. Two would be very sustainable and productive.

Alright, so seems like your sticking point is moving too slowly. I prescribe to you:

Also, why not give cold approach another try? Plenty good guides for that on GC too. You live in a big city? Great! You'll find plenty matching your "criteria."
 

raiden

Space Monkey
space monkey
Joined
Oct 1, 2020
Messages
132
No. Pull after first or second. Otherwise, write her off. Also get an apt bro. No more dates till then. You're 30-something dude, looking for marriage, and living with the folks? Wtf??
My philosophy is to never write anything off. I keep pushing until I get dumped. Never give up and all the rest of it. I need to save up a lot more to buy an apt. Very best case I'll be able to do it in 3 years.
20 dates a week. Kidding, but for a year is ridiculous. At least, at LEAST one a week. Two would be very sustainable and productive.
So I should be aiming for around 50 dates per year? That seems like a lot and hard to sustain. I guess if I can count these singles events as dates too then I can get to maybe 40 per year. That's along the right lines. It gets tough and boring but I guess that I just need to put my head down and do the work.

Alright, so seems like your sticking point is moving too slowly. I prescribe to you:
Yes I have seen that article but I don't see how I move things forward when I am on a date and I sense that things are going well but the momentum is drying up. That feeling of the momentum drying up means that I should have already moved things forward. But how do I move things forward in a situation like this?
Also, why not give cold approach another try? Plenty good guides for that on GC too. You live in a big city? Great! You'll find plenty matching your "criteria."
I could try cold approach. I wanted to start with these singles events. I found them easy and had no approach anxiety so I feel like I am as ready as I can be to start cold approach if I want to. But it's a big time and emotion drain, and I'm worried that I'll just have the same experiences as I did at the singles events. With my looks and fundamentals, I know that cold approach is going to be very very tough for me. My feeling is that I have a chance on the apps because I have all this personality stuff in my profile and some possibly good prompts to make up for my deficient looks. But in cold approach you can't use the fact that you're an intellectual or that you like board games or fine art. You make your opener and the woman has to accept or reject you before she gets that information. Is my understanding of cold approach correct or could it go differently to the singles events?
 

Skater

Tool-Bearing Hominid
Tool-Bearing Hominid
Joined
May 10, 2024
Messages
54
My philosophy is to never write anything off. I keep pushing until I get dumped.
Can't get dumped if you don't have a relationship. Better to cut your losses and start fresh than desperately chase some chick. Logistics will screw you though, consider renting.

It gets tough and boring but I guess that I just need to put my head down and do the work.
You're right, it is tough and boring... with that attitude! Ideally, you should actually like meeting, talking, and sleeping with women. Obviously. Crazy part is this will make you more successful too.

I don't see how I move things forward when I am on a date and I sense that things are going well but the momentum is drying up. That feeling of the momentum drying up means that I should have already moved things forward. But how do I move things forward in a situation like this?
By taking the lesson, then escalating anyway. If it "doesn't work," chalk it up and try again with the next one.

My feeling is that I have a chance on the apps because I have all this personality stuff in my profile and some possibly good prompts to make up for my deficient looks.
What are you talking about bro?! Looks matter more, WAY MORE on the apps. Of course they don't hurt in cold approach but you can bury them in an avalanche of personality and emotion in person because they're really not that important to girls, unlike to us.

But in cold approach you can't use the fact that you're an intellectual or that you like board games or fine art. You make your opener and the woman has to accept or reject you before she gets that information
You can by rigorously learning from field experience. The opener itself would only disqualify you if you go very direct. Look into indirect strategies.

The singles events could work but you have to escape the "dating event for hopeless people" frame to really do good. Pretend, at least to yourself, that you randomly stumbled upon this preponderance of hot(?) girls and chodely dudes and run game as usual.
 
the right date makes getting her back home a piece of cake

raiden

Space Monkey
space monkey
Joined
Oct 1, 2020
Messages
132
Can't get dumped if you don't have a relationship. Better to cut your losses and start fresh than desperately chase some chick. Logistics will screw you though, consider renting.
But I mean, shouldn't I go on any date with any woman who's willing to go on the date with me? I need the experience, right? And when I eventually do get dumped i.e. when the woman finally terminates the sequence of dates, I can do a post-mortem to see what went wrong. With all of my costs and bills, I don't think that I can even afford to rent right now.
You're right, it is tough and boring... with that attitude! Ideally, you should actually like meeting, talking, and sleeping with women. Obviously. Crazy part is this will make you more successful too.
Dates are boring...! And the ironic thing is that I'm getting more first date to second date conversions now than I was before 2023 when I found dates more interesting. So for me at least, being bored on dates has been a good thing.
By taking the lesson, then escalating anyway. If it "doesn't work," chalk it up and try again with the next one.
I still don't get it. Say I'm at a coffee shop and I think that I see an escalation window, and I also see that the date is about to start losing momentum. Being an avid GC reader, my first guess is that I need to take that escalation window while it's available or else the date is dead. But what do I do at the coffee shop?
What are you talking about bro?! Looks matter more, WAY MORE on the apps. Of course they don't hurt in cold approach but you can bury them in an avalanche of personality and emotion in person because they're really not that important to girls, unlike to us.


You can by rigorously learning from field experience. The opener itself would only disqualify you if you go very direct. Look into indirect strategies.

The singles events could work but you have to escape the "dating event for hopeless people" frame to really do good. Pretend, at least to yourself, that you randomly stumbled upon this preponderance of hot(?) girls and chodely dudes and run game as usual.

What I have found is that I seem to get more attractive women out on dates from the apps than I do at these singles events. I haven't tried much approach recently outside of these singles events. But at these singles events it seems like it is much tougher for me than at the apps. One example is this. I was chatting to a girl and she was asking where I'm from etc. Then she hit me with the "how old are you" question and soon after I answered she had to go to the bathroom. When she came back from the bathroom she didn't come to find me so I knew that my approach was a failure. But she was 28 and I know that 28 is definitely not too young for me, based on the ages of the app women from the past year or two. Another example is this. A girl I saw at the event looked almost exactly like a girl I am scheduling a date with from the app. My friend even said that there's a strong resemblance. The girl from the app seems happy to come on a date and I expect that she'll have a good time. But the lookalike girl at the event was being a bit flightly, not agreeing to move with me. Then when I suggested to take her out on a date to show her the city, she said that she'd rather go with her girlfriend. Now I know that the age thing and the mention of going with her girlfriend can both be interpreted as tests that I should pass. But the point is that these women are making things much more difficult for me than the app women, and they don't seem to be very different.

I am already treating the events a bit like cold approach night. I am trying different direct and indirect openers. But what I'm finding is that I am accepted or rejected right away once I have delivered my opener, based all on my looks.
 

mirror

Space Monkey
space monkey
Joined
Jul 8, 2025
Messages
197
Hi all. My dating goal is to meet a woman with whom I can settle down and have a family. I'm a mid 30s guy and I want to meet a woman satisfying these things. Under 30 (most of the women I dated were this age and it felt like a good vibe, plus I want the best chance of good fertility), into health/wellness (because I am), not a heavy drinker and not too curvy.

Go for any woman <40 and you will be fine fertility wise (there is conflicting research at better outcomes at children). I think it's easier to settle down with women between 28 & 35 in general, since they are actually looking for commitment and children by that age.
 
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