I am wondering how much he played with her emotions versus how much she didn't land him and got upset?

We don't know as this is all very second hand but she was very serious only interested in marriage and they did not have sex it would appear. What is a very serious and respectful man to do in this situation -spend time with her and see how things develop. He didn't rush in and introduce her to people because he wasn't yet sure. He didn't see things developing the way he wanted, so he dropped her. This is not bad behaviour it was an all or nothing offer on her side and on reflection,, he chose nothing.

While it might be fair to say he could have been leading her on if he was having plenty of sex with her and keeping options open by refusing to go non exclusive, in this case he was not getting anything from her but the work of staying in touch and setting up dates and driving to see her and such. This is not something you will do for someone as fun or as charity. He was still interested in her as a marriage prospect until he wasn't.

The thing to do would have been to talk about exclusivity and when it comes in in their specific case of not having sex and talking about marriage only. If no promises were made, it was just a high stakes situation, she risks a year of her youth hoping to land a rich man (not idea if she was of a similar background herself or how compatible his richness made her). He risked losing so much if he married the wrong one. Likely as not the right answer was reached. Play high stakes, you can be hurt.

Actually, in Eastern Europe, and even much of Western Europe back in the 1990's, it was the norm for women to dress and look "hot" right up to their 40's. The key was that they did understand that if you wore "hot" clothes but were out of shape, it would make them look silly so this motivated them to stay in shape.

Perhaps if this "hot mom" dressed in wal-mart approved sweat pants that wouldn't make his friends wolf whistle anymore, but she might let herself go.

There's not just being in good physical shape that allows a woman to do the "hot mom" thing, but also general stylish choices such as low numbers of tattoos, no face piercings, and properly colored and styled hair. I've noticed that once a woman gets a face piercing, they start to let everything else go as well.

That said, the guy should rock it like this. "Hey Jake! I heard you brought your mom to the prom!"

https://www.youtube.com/shorts/cqwSwb8TCI8

Black and white is rare in life and never found in women or men. You add together a basket of facts -pluses and minuses and decide if she is worth the commitment of a LTR. There are actually very few deal breakers -being a professional whore is one, being a drug addict, being a thief form family are others but a hook up is a big minus but not a deal breaker.

Remember almost all woman are vulnerable to seduction by the right man at the right time. Its why in the past girls were chaperoned. If boys and girls are left together with no social consequence, girls will be seduced even sensible ones, some by scoundrels. In today's society there is no social consequence, so expect desire to be given in to in suitable conditions. This is why its best to get them fairly early before they make too many mistakes or develop too many bad ways of looking at men. You are young and this is a lower risk. You may risk losing a good relationship by excluding her on that alone.

It might help to try looking at this from another direction. So you meet a girl with no hook ups and a body count of zero to 2. First question to ask is "Why so little sex?" Is she unattractive? Ok she is not, then is she one of those girls who don't like the idea of touching wieners, who don't want cum inside them, who think kissing is a bit gross? Do you want one of those girls in your bed every night? Ok She is attractive and has a healthy desire level, so is she a religious freak (not a church goer who wants to be seen as virtuous or a believer who sins sometimes but a real believer with the self discipline to keep in line? Do you think this would be a good match for you and your personal ethics? OK she is not and likes sex and is not excessively religious or obsessive about chastity over enjoyment of life, so is she very sheltered and has had no opportunity? If so, you might just have hit the jackpot but do check that your background, ethics and ideas of the importance of family fits well with hers because as she becomes less sheltered, she will see these things matter and do check she is not mad or an evil bitch who drives men away. If she is not very sheltered and she is hot and loves sex and is not a god freak or a bitch, then maybe she is just a lair? Do you want a lair in your bed, someone who lies about who they have done it with when you know she will meet other men more attractive than you? Ok she is in fact a virtual unicorn, she is hot, loves sex, not religious, not sheltered and not a bitch, not a liar, she is just focused and wants one man for life. So what is she doing with you with your lifestyle and history?

These days chastity is not rewarded by society so there will need to be a darn good reason for it. You can screen for promiscuity but the absence of perfect chastity is normal in the sort of woman who makes a good mate unless you meet her when you are both starting out in life.