To be frank you're asking too many stupid questions in this post. What is going on? Have I blown my chance? Does she want more?

WHO CARES

You are 29. She is 39. She is also going through a divorce which means she is still technically married!! WTF man, you're actually agonizing over your status with this woman when she is still legally married? She needs to be kissing the damn ground you walk on because you are both younger than her and have taken her to pound town. She is going through a damn divorce, I do not give a shit whoever it is, divorce is serious business for anyone to go through and is emotionally draining. She is not going to be anywhere near ready for a serious, real relationship for at least a year after the divorce is finalized in court. Read that again if you don't understand: finalized in court. Meaning a judge has signed off on it.

You need to go bang a couple of girls around your age range within the next week or so and make sure she knows you're seeing other women. Stop getting so worked up on this nonsense with this older woman, she can't even give you straight answers about what's going on in her life right now, dodges questions, and generally acts vapid, like most women do. Tell her to bring a friend next time she wants to bang.

When I see a cute girl and feel the urge to approach (I have zero approach anxiety thanks to approaching hundreds of women), I end up cockblocking myself.

Internally, I think I’m not man enough. It’s not about her. It’s not about that one person. I know I can pull the woman I’m approaching—hell, I’m already flirting, having fun, and staying outcome-independent—but I don’t ask for her number, and I don’t even want to have sex with her. It feels like too much hassle.

It’s not that she’s out of my league or that she’s so beautiful she’ll reject me. Who cares? What really bothers me is that I know my potential. I was once in incredible shape—mentally, physically, and spiritually strong; resilient and disciplined. I think this goes deeper than women. I want that man back. I need to work on this.

What’s your opinion on this? I’m not looking for advice like “approach more” or “fuck more.” I want to keep this philosophical. Is there anything I’m missing in the bigger picture?

Ps. I had a lot of partners in the past, I know what woman is, what sex is, what abundance mentality, spinning plates, oneitis is etc. These are not my problem.

You have another woman and this woman is 10 years older than you with kids and emotional baggage. Do get your priorities straight. This woman, if she lets her guard down -and it has slipped already- could end up being a major thorn in your side if she falls for you. You know it will end badly and then she will end up saying to your friends how badly you used her when she was vulnerable.

You go lucky she is backing off but it seems you also got bitten.

I would keep your distance, tell her you agree she is vulnerable and its best to stay friends and move only very slowly if and when she likes. This gives her confidence. Then let her come to you while you just act friendly until her guard slips again whenever. You have no need to care when that is, you are in a surplus situation. But if you try to make things happen and push through her fears, it could go two ways. She could run away or you will end up being the one who hurt her in her eyes and why bother with all that drama in your friends' circle even if you care nothing for her.

There is a lot to unpack here, but I ask you this: What are your intentions with this woman? Are you aiming to commit to a 39 year old woman who has two kids and is going through a divorce? If yes, why? Have some self respect, man. I don't care if she looks like Jennifer Anniston. 99 times out of a 100 that is a terrible idea that is going to be a disaster... I'll quote Rian Stone here... "single mothers... a terrible situation that's not my problem"

If your answer is no, and you are looking to plate her, I actually have a plate at the moment that is a single mother. Initially, the single mother I have plated LOVED the idea of casual sex, noting "it finally means I'm moving past my ex". For a while now though, it's "I know what I deserve for my daughter and myself" and she has distanced from me. The glimmer of the validation wore off. Plates always break eventually. Women have their own motivations as well, and it seems that this 39 year old woman that has two kids probably lives life compulsively pursuing and much heavily prefers relationships as her base state despite probably genuinely wanting to fuck you and probably does enjoy the validation. Call it conflicting motivations. You told her you "don’t want kids or marriage" as well as you not having kids probably smells of bachelordom, so if she is wired to compulsively pursue that, that part of motivations for her may understand pursuing you is not going to accomplish her goals.

I would let the situation cool off, play it cool, and wait for the next opportunity to be around her in person, break the ice yourself, and game her like you have been.

Finally, I'd be careful closing a girl that is giving mixed signals on whether she wants it. A little post-hoc regret from a woman is all it takes in 2025 to end your career and your social life. If a woman seems even sort of iffy on fucking, pull back the reins. Though I may be stating the obvious in saying that.

Met with a milf for drinks. Flirty vibe. Kino'd. Invited her back to my hotel (30 min away) but she said she has to go on a work trip tomorrow morning which she told me about before. She seems interested in meeting again over text afterwards.

fair enough

She said she doesn't do that on the first date and she got out of a relationship recently where she was left with a lot of trust issues etc

absolutely fucking not. NEXT.

Here's the red flags:

• no kissing
• in your bed but blocking sex
• not reciprocating

and worst of all:

The "beta bait" of "my ex boyfriend blah blah blah trust issues".

Don't fall for that shit.

If you give her the 6 months of comfort that she says she needs before you can kiss her, she'll fuck some guy she met at a party before you get a chance to.

The whole line is a disgusting lie, it means "no sex for you, but please do keep the attention and the back rubs coming until Chad gets me".

In the nicest possible way, you gotta always be thinking "fuck me or fuck off". She might need a date or two, but if she's in your bed and won't kiss? Yeah... NO. fucking next her, with prejudice.

Background

• I’m 29. Lots of relationships, always end as it don’t want kids or marriage. Currently in an open relationship.
• she is 39, two daughters and going through a divorce
• met her via mutual friends. Over the last few months we gotten close over various social events. She doesn’t come to much as she is busy but she always comes when I’m 100% certain to be there. She gets very jealous when other girls speak to me.

Party and sleeping with her

• we was at a party, we spent all night together. We kiss slightly a few times but she pulls away. She says I have a girlfriend or that everyone is watches
• she tells everyone we are just friends.
• we separate but I hear that she is looking for me. I find her, we kiss and make out.
• we get a hotel room and we sleep together.

Mixed signals from her

• she tells everyone we are just friends
• while kissing and making out she says she can’t do this as she too old for me. She has too much baggage with children
• she tells me she never wants to lose me as a friend. I’ve become invaluable in her life. I’m a high point for her.
• she said she can’t be with me as I don’t even want to get married. She pulls away from kissing. I lean back and she says your not even fighting for me.

I call her the next day

• I call her to she how she is and what she wants. I tell her are we more than friends? She says she wants to keep things casual as friends. And see where this goes with no labels.
• she can’t jump into things as she never has much time with full time work and having two kids. She said is going through divorce as well.
• she doesn’t want to jump into things and ruin our friendship. She doesn’t want to lose me from her life as she wouldn’t know what do without me.
• she says she barley has time for anything and she can’t just drop her commitments for me.
• she said she has a fear of getting hurt.

What is going on?

• have I blown my chances by asking if she wants more?
• what does she want? Does she does want just friends or something more.
• is she afraid that I’m younger and therefore could leave at anytime? Thus losing me all together?

What should I do?

• when I next see her act like it never happened and just flirt and be friends like before or maybe ignore her and let her feel what life is without me?

So women give me sexual IOIs

Will this is the thing. It's not really "sexual IOIs". This is poor naming from the TRP community.

Women wouldn't be imagining having sex with me or "playing" with me if I wasn't at least a prospect.

You don't understand women - and you are looking at this the wrong way.

I'm getting back into approaching. I live in the suburbs and I'm comfortable here. But it's not great for getting loads of dates.

I have around 20 approaches in a suburban area. Most nos and I got 3 flakes. I just text logistics.

Right

What's the ratio of how many women I'll have to approach? 100? Cause God damn. Its not like a city where you can cold approach 50 in a day. Suburbs not so much. Maybe 3-5 a week.

About 30 to get laid, if you're reasonably good looking and reasonably good at it.

Half will talk to you.... half will swap numbers.... half will flake on first date....... half will flake on second date...... half won't sleep with you after that.

Don't get too autistic with the numbers, but 5 halvings leaves you about 3% "lay to fuck" ratio. And that's if you're good.

Maybe half of women are somewhat available (no bf, unhappy with bf, slut, etc).... maybe half will like you....... of those, some will see someone else or logistics just won't work out. Everyone has a life, attractive women have options.

A lot of those "failed" interactions will be fun, and when you fuck them it will often be lots of times, so the 3% ratio is much better than it seems.

But something isn't right here.

If women are checking you out, then you are right to think you are basically attractive enough.

But if you are hearing "I have a BF" every time, then you're approaching wrong. If you're hearing it half the time, then it's all good.