Older Woman. I'm 21 and she is 25. We went to high school together and I was a freshman when she graduated. Is the difference in age still as big of a factor?
Ok, feeling like a waste of time question here- so sorry it's not straightforward-advice-ready.
We were moderately good friends in HS, well more of acquaintances, but we spoke regularly. It was a very small catholic high school (I graduated with ~38 kids) and so the opportunity for interaction with upperclassmen was high. I switched from public school and knew no one so I became friends with older guys on the football team because I was a starter and by association made friends with many older upperclassmen. Anyway fast forward 4 years and a few off and on interactions and you've caught up.
I'm still in college and so is she- she went for a year then went to a community college for a few years and now is back in school at another university (not mine)- and I am in a 5 year program. She has a year left and I have a year and a half left. Part of my program involves working for a large corporation in our hometown and she babysits in the downtown area so we run into each other frequently. I never had the nerve to ask her to lunch properly because I thought she viewed me as a young pseudo-friend that she knew from high school, so we'd always just chat in passing.
We are both phenomenally sarcastic and it's a riot to have a conversation with her.
This past thanksgiving break I was in town and at a local bar with some friends (so happens to be owned by a mutual friend and the father of the children she babysits for, irrelevant mostly) and I was bombarded by about 50 people from around my graduating year that i ran around with during hs. So I was a bit tired of having the same convo over and over again so I dropped down to another area of the bar which just so happened to be where she was hanging out for the same reason. So we chat it up, as much as you really can at a loud bar, and have some laughs. I casually mention grabbing lunch when she comes back into town or something, she's all for it. Cue drunk friend/awkardness introducing me to her older friend she was there with and end of that interaction.
So a couple weeks go by and I am checking something on facebook, yes facebook, and yes i know it's lame- but everyone has it.... yea whatev. Anyway- her name pops up on one of my friend's walls so I check it out and add her. Thought it kinda odd that she had it, but that's not really fair for me to say. So i leave a comment and then I check back later and see her screen name so I add that, and sure enough she's on. I im her and she knew who i was with out me saying... so that means she had my screen name from high school which i thought unlikely or she added it, either way i can't see that being a bad thing. (Wow reading over this if feel like a 7th grader talking about screen names and facebook...)
So we talk on aim, and we talk a lot. She lets me know when she's heading into town and I leave her my phone number to call me when she wants to go, because I'm available pretty much whenever. So she does, and we go- we've gone 3 or 4 times now and all of them have left me late returning to my job- not a big deal but odd because the conversation was that good. I love chatting, but I rarely feel like I'm connecting with people because I'm in a different mindset than most people my age and most people regard me as more mature (and always have...)
So we've talked about dating histories somewhat in passing, i'd met her last one when I was working before and know the details of how that didn't work out. She knows some of mine. I've been single for 2 years now with the exception of a few little flings here and there, but have felt open to the idea of dating again for awhile now- just been way too busy to meet people.
Anyway- My question basically boils down to A) Would she feel like she was being judged for dating down? B) Would that ever change? C) How do I approach crossing the friend barrier?
As info, she doesn't drink or do anything like that- we've talked about the reasons and I admire her for it, I on the other hand could probably be considered a functioning alcoholic (aka college student) and do enjoy drinking in moderation, but frequently. I'm not the sloppy drunk, and I really don't change at all when I drink- I just get a little more lively and I've never had any problems with doing stupid things or being irresponsible, in fact i'm always the responsible one... so I don't think that would be a problem. We're separated at school by ~2 1/2 hours and our mothers worked together back in the day.
Oh and I have no idea if she would read this- if so I'm certainly never going to stop hearing about it... regardless of outcome. So if you've got experience with cougars as we call them (older women) please share.
Now that I've said the read disclaimer- I'll also add she is not my type per say... not that I truly have a type because I think it's an unnecessary filter... but she is a moderate redhead with freckles and looks similar to the chick on love actually that is a porn star or whatever acting that's for and i typically go for the smaller tan skin dark hair thing.
yea that was long, sorry.
B) No.
C) Others will no doubt give you a longer answer, or you can find similar questions already on AskMe.
posted by Partial Law at 2:24 PM on December 26, 2006