A Woman Speaks: Should I give up on this man?

[Lilly]

I’m a 23 year-old woman. Zero romantic or sexual experience.
I‘m into a nerd-professor type of man who’s approached me several times, initiated physical contact, unbreaking eye contact only, generally shown interest in a clumsy (romantic aggressive) way. This site has given me lots of insight on male psychology, but due to Corona I need specific information.
He’s 30 years older and lives together with his (ex?)wife and the youngest of their three kids (no wedding ring on either of them, she behaves coldly towards him and he made it clear that he’s not been happy in his marriage, they have separate last names. Either way: he was attracted to me).
With GirlsChase I realized that he’s done some correct things, but also made lots of mistakes, which explains my past-year’s expiration of attraction. He wasn’t consistent/dominant/skilled in the game enough.
Then Corona separated our venues and a few months ago they posted a group picture. He got super hot (lost weight, looks younger) in that dorky way I like about him so much. In January he’ll give an online presentation and he knows my name, so I’m considering joining that presentation and seeing if he uses that possibility to reignite things.
As you can see, I really like him still.
Should I “re-approach” by showing up in that online presentation and use my new knowledge to give him another chance (e.g. recognize when I want to auto-reject)? Or would I be better off waiting for a man who’s more adept at the game?
Side note: Please no “he’s too old, so forget about it” comments. I’m into older men.

 

[Mr STIF]

Since you asked me. I say give him another chance as your intuition has already told you. If he doesn't take the bait then you can take the second option which is: finding a Man more adept in the game.

 

[Zoro]

If he's 30 years older then I would bet he's hesitant to make a move. Even if you both are ok with it, it's still seen as taboo to some. He might be thinking of his reputation in his career and with his peers. An older man making a bold move with a younger girl is the type of stuff you see on headlines.

I would say give him another chance, but keep that in mind. How can you drop some strong hints that still feel good to you. Many women think their hints are obvious when they are actually really vague. Of course, the ideal is finding a guy who picks up on these, but we're talking about your nerdy DILF.

You could also give him some strong motivation to overcome his hesitation. If you're looking SO good at the presentation, drop some hints that make him think a little, and give him an "in" with plausible deniability (hey, I have some questions about the presentation...), AND somehow let him know things between will you be discreet, then idk what will get his attention.

No girl likes to have to spell it out for a guy, so I tried to give you some creative things to work with. But I think those four parts might work real nicely together.

What do you want with this guy, a relationship or just some DILF D? Because that makes a difference too. What kind of hints to drop...

 

[Lilly]

If he's 30 years older then I would bet he's hesitant to make a move. Even if you both are ok with it, it's still seen as taboo to some. He might be thinking of his reputation in his career and with his peers. An older man making a bold move with a younger girl is the type of stuff you see on headlines.

I would say give him another chance, but keep that in mind. How can you drop some strong hints that still feel good to you. Many women think their hints are obvious when they are actually really vague. Of course, the ideal is finding a guy who picks up on these, but we're talking about your nerdy DILF.

You could also give him some strong motivation to overcome his hesitation. If you're looking SO good at the presentation, drop some hints that make him think a little, and give him an "in" with plausible deniability (hey, I have some questions about the presentation...), AND somehow let him know things between will you be discreet, then idk what will get his attention.

No girl likes to have to spell it out for a guy, so I tried to give you some creative things to work with. But I think those four parts might work real nicely together.

What do you want with this guy, a relationship or just some DILF D? Because that makes a difference too. What kind of hints to drop...

Concerning the first point: True that. My family knows I'm into older men, and their opinion is what matters to me most. Concerning his view on the age gap: He initiated brief physical contact (initiating a conversation, pressing his side into my arm, holding there, retreating) at a uni party with my peers and his colleagues everywhere. He either doesn't care or is completely dense to social norms.

Fun fact: I read some articles here on signs a woman likes you. I indeed only did some, like play with my hair and eye contact (and 'coincidentally' sitting where he has a chance to talk to me, which he did). I admit those hints I gave him were vague, but they felt huge to me (again: zero experience with this).

I don't know him enough yet. He has disqualified himself as a one-time shag though and is in the long-term zone. As a woman, I've been checking him for long-term potential, naturally: he has a proven streak of monogamy, raised 3 kids with a woman, has a good steady income, we have similar interests, he provided for me (context appropriate stuff like cooking, getting up to fetch me more water, offering me other drinks which I accepted) when I was at his home because of an official work-related thing.
Also as a woman: What I want is for him to be attracted to me, to make his interest consistently clear, for us to get to know each other and to commit when we both think a relationship with each other is the best option.
But since I don't know him well - and he has no idea I even still think of him - I'm a "Curious Girl". I want to get to know him without forcing it or becoming too active/masculine.

 

[FunkMaster69]

He wasn’t consistent/dominant/skilled in the game enough.

Hi Lily: Welcome to GC

J Wick is right ... It's very unlikely he's going to make a bold move. Especially with the Me Too movement ... it's literally neutered some men. A lot of my friends nowadays are scared to be masculine... you heard how a few hundred men lost thier careers right? Maybe that's why he's so relaxed now? I use to be a university student at a top 10 uni. I basically led a double life. At Uni I would be boring, because I was thinking of my reputation. There would be almost a zero chance of me making a bold move in a large lecture or anything. At a party, well I'm drunk... and it's a party.

Second of all, he's divorced and took off his ring. To him it's just a relationship of convenience and/or out of respect for his child.

Thirdly, it seems that you like him. So ima just say this. Go for it. You should ask him out. It'll make you stand out. Tbh, some of the woman that I've liked the most were the ones that came on to me. Those are the ones that stood out and I remember. The thing is I've approached and asked out a lot of woman. And it gets old quick. One time I was at a mall and a very sexy woman approached me and asked for my number. I still remember her. It happened again at uni and well I remember her too. Out of all the ones that I've asked out, I probably remember like 5 of them. Less fondly tho.

If the guy has a job and a kid, it's very unlikely that he'll ever turn into a guy like us anytime soon. He's just too busy to actively work on his social skills and learn game. Plus, you have to realize this. You're a virgin and this is a huge deal to you. This guy has probably gotten laid a lot, has had a few gf here and there and so it might not be the biggest deal in the world to him. If things don't work out between you guys, he probably has an ex or a colleague he can hit up. You on the other hand are thinking long term... Either way you should fuck him and lose your V card. Even if things don't work out with our DILF, you'll still have the experience of fucking a man near his prime. Since he's previously married, you can expect it to be very good sex. You on the other hand don't bring much to the table other than the fact that you're a virgin. And after the first time you have sex, you'll lose that card... but tbh your going to be pretty bad at it. It's going to be like playing basketball for the first time in your life.

Lastly, there's more to life than game. Sure you might meet a man who's better at game, but it's unlikely that he'll be a DILF. And he probably won't be the nerdy professor type.

Tldr; this is a way bigger deal for you than it is for him. You should make a move because it'll make you stand out as he's probably use to approaching woman, but not used to woman approaching him. Even if things fail, you'll have been gotten laid by a man who knows a thing or two, vs a man your age who'll probably just hump you for a min and then bust...

 

[Lilly]

Update: After four more-or-less chance meetings and chats (with me even telling him he’s allowed to contact me, at some natural point in conversation), he didn’t take the bait. The great thing? He’s obviously loyal to his wife which counts more than anything, for me at least.

 

[William Wallace]

i'm gona be unpopular guy here but. just so you know

Update: After four more-or-less chance meetings and chats (with me even telling him he’s allowed to contact me, at some natural point in conversation), he didn’t take the bait. The great thing? He’s obviously loyal to his wife which counts more than anything, for me at least.

 

[Lilly]

i'm gona be unpopular guy here but. just so you know

I suppose you want to tell me that a man around his age (statistically) needs 2 premarital partners for his chances of divorce to rise significantly? Good to know I guess! But - contrary to the personal evidence the authors of GirlsChase experienced - I’m a bit of an outlier in that I’m not attracted to “cock-sure” men who gained experience with multiple women anyways.
Thanks for the chart!