A good quality I have is that I'm usually well-prepared going into something. In a couple of days, I'll be going on a coffee date with someone I really like (obviously); we really connect well. I haven't been on a "date" yet in college, but that's not what my worries are about.

It's pretty certain this girl is going to ask questions about my past and then about some social things here. I do pretty well for myself now, but I have some holes too (especially in the past). I have no idea how to best word this so it doesn't make me sound AFC:

-I am a lot different now than I was back in high school. For starters, I look a LOT different. I used to be a real scrawny-looking kid who was looked down upon by peers. Now, I've put on a lot of muscle (to the point where people think I take supplements) and I have really improved my physical appearance. Additionally, I am much more confident and can stand up for myself whenever needed.
-I couldn't get a girl to save my life back in high school. Any girl I asked out laughed and said no in a harsh manner, I couldn't get a date to my Senior Prom, and something must have been said about me because girls from my high school class STILL give me glares and whatnot. In terms of relationships, I couldn't get one in high school; I haven't really pursued one yet in college (have only asked out a few girls)...in short, not much experience with women.
-While I have a close group of friends back home, I only have a couple close friends here at school. By some odd coincidence, three of my better college friends have transferred to other schools, so I don't see them much anymore. Also, with Frosh/Soph going to the parties (I don't know a lot of Sophomores) and Seniors hitting the bars because they're 21, I'm in a strange spot as a Junior here. Usually, I have to get creative, meaning heading to the movies with them or every once in a while, actually finding a party in this not-a-big-party-school-at-all campus.

I feel I'm pretty good socially in that I can talk to anyone and be myself (I'm complimented for my "people skills"). I can get people to laugh and we all have a good time. However, I don't have a big group of close friends in college, and I don't really know many girls real well (just a lot of acquaintances). So what I'm asking here is, if this girl asks, "How was your last relationship?," "What do your friends and you do every weekend?" or anything of that sort, how is the best way to go about it without seeming strange?

I should add that this "date" is tomorrow

For what I wrote in the main post, I don't think the lengthy answer would work for the one in red, and I don't know how to get around the green and the blue parts.

well im no pro at this but ill give it a shot

How was your last relationship?
just play it cool and say well it just didnt work out between us, she cheated on me~gives you sympathy ( im not too sure about this one though)

what do you and your friends do?
well we like to go skydiving and jump off cliffs you know nothing special with a wink , if you do this right you could pull it off though ive never tried it haha

goodluck

I don't think any of the real answers sound weird at all.

Same here.

Although im 24, and I have had a decent amount (20 lays), just never took anything to a serious level. So I end up sounding like a man-whore or loser.

You've had sex with 20 girls? That's actually a lot compared to the overwhelming majority of guys.

I would tell her the truth! It's so much easier and you won't have to worry about explaining anything in the future.

I've learned that *most* women are understanding enough to accept things that happened in your past. Just be genuine, try not to come across as creepy...oh and make her laugh!!!

Women are people too with their own pasts, and problems...If she calls you out on something have her tell you an embarrassing thing in her past and if she won't then tell her that that's too bad bacause you frown upon dishonesty....now go easy on her if she's really shy!

Unless you're a serial killer, rapist or you're into little kids...you'll be fine as long as you're confident!

-Crain Diesel

Seriously dude, please don't give advice that you haven't tried yourself first.

The answer about her cheating on you is bad because it sets the girl with the frame of mind that girls cheat on you. This is bad.

The skydiving/jumping off cliffs thing is fine.