Is it true that men automatically assume if a girl has been single for a long time that she's crazy or something is wrong with her?

Kind of.

When I was in college, I dated this really really really pretty woman whose life goal was to get married and have babies. She was extremely selective about guys, shut down every dude that tried to talk to her because they were too this or too that or not enough whatever. Mostly her excuses revolved around the idea that no one fit her ideal for a husband and father of her children. Her parents had basically spent her whole life warping her expectations and telling her she was this ungodly special and beautiful creature that no one but the very best of the best should even be allowed to speak to or buy her a milkshake at Sonic.

She'd never even had a serious boyfriend or let anyone get to second base til I came along. And she was 22. 22!!!

I was flabbergasted because I'd been dating banging strippers and barmaids who, at maybe 18 or 19 had already been through a slew of guys, could kiss and give head like a porn star, and were frankly quite emotionally grizzled.

Dating this chick was like dating Kimmie Schmidt. She was dorky and precious and just kind of stunted in a sense of maturity.

She was used to guys being overwhelmed by her looks and her demeanor, and the douchebags ( I also might have been a douche back then, but not a hardcore one) instantly got the "I don't put out" vibe from her.

I got past the defenses because I had a lot of confidence and didn't stare at my shoes and mumble the whole time I was talking to her.

But she was weird from being single so long and not having a relationship. She didn't know how to act. She didn't know how to handle any kind of conflict. Every time we communicated she was on the phone with her mother asking for advice like "Hey, he just asked me if I want to meet him in the caf for lunch. It's like the third time this week. I really like him and we have fun, but is three times a week to much for lunch?"

So, yeah. There's a reason sometimes. But you have to give things a chance and not paint a scarlet letter on a woman just because she's been single a long time and is kind of weird. You're kind of weird. You still want someone to put your penis in their mouth. Just be cool, like a little Fonzie.

/r/AskMen Thread