I'm in my late twenties and, like several of you, have never been all the way with a girl. Since the onset of puberty I've been severely depressed and hated myself to much to love someone else.
But now I've left my awkward stage and I'm gorgeous (not my words). So, I took a co-worker out on a date a week ago (bad idea, I know.. and she's not even a peer). She's not the youngest or most stunning that I could have had, but she is young and stunning. Despite needing two hands to count how much younger than me she is, I'd run out of fingers and toes before I could tally the experiences she's had (not all of them men). After one and a half dates, we have shared all this with each other, the sordid details of her most shocking sexual encounters and my most personal issues (which I have never shared with anyone). But she appears as ashamed of her sexual history as I am of my lack of one.
She has insecurities issues. The fact she had all of these sexual experiences, and then she disclosed it to you on the second date is a big warning. I would be careful with her.
> On top of this,
This was to end: she's currently seeing someone else. She told me during dinner and felt really bad about it. I think we're both fucked up in the head.
Maybe she's the right person to pluck you out of your shell. You're both damaged goods, but maybe both of your unbalanced chemistries can somehow perfectly complement each other.
So do get laid, and expect a bumpy road ahead. That's much better than living in fear and never doing anything.
I've just clocked past the twenty mark, and personally I wouldn't date a guy more than 5 years older than me, simply because of the different priorities in life. But I do have a best friend who sounds just like the girl in your post. At one point she'd started seeing a 30 year old co-worker, before completely finishing a relationship with another considerably older man. She never got serious with the either of them, whereas I sense that they were looking for someone to commit to. My point is, other than sexual gratification, I don't think it would do you much good entering a relationship with any kind of expectations with a much younger girl.
Okay, so you're possibly inviting some masochism and dysfunction into your life. But you LIKE her, don't you? And it seems like you know what you're getting into.
Stop second-guessing yourself. Just because you're not so young anymore doesn't mean you can't do things by the gut.
It's done. It's final. And I'd do it all over again.
I don't think I could have ever found anyone more sensitive about it.
If she wants to stick around I'll be content, but depression has a way of keeping one realistic so I won't be shocked if she doesn't.