Sooo, theres this girl, my age (19)... want to take it to the "next level"?

Question

I've been acquainted with her for about 8 years, really started talking and such this year, and i dont want to ruin a young friendship if she doesnt like me? wont it be awkward after i ask, if she says no? I also know her brother, to add to the whole 'awkward' feeling...fun? Not really.

...Oh, did i mention i cant call/ email/ write because her mom is super overprotective? All avenues seem blocked, but i dont want to give up? Starting at the same college as her next semester, and going skating w/ youth group (that shes in) on the 26th...best time to tell her, and how? sorry for the length. =/

Any help greatly appreciated. If you need more details, tell me. =)

I'll wait as long as i have to, if thats what it takes.

Her mom is basically set into the "My house, My rules" mentality.

Answer 1

If your afraid of it being awkward if she doesn't feel that way for you then just flirt & drop hints and see how she reacts. If she seems offended tell her sorry, you were just kidding around. If she seems flattered or starts flirting back then ask her out. Her mom can't be overprotective forever & since you have known her so long, I would think if you 2 started talking you would be allowed to see her. Just be respectful and nice to her mom.
Knowing her brother could help you out. Buddy up with him & maybe you could go to their house! Don't use him of course, but it would get you closer to her!

Good luck!!

Answer 2

She's 19 & her mom is still controlling her? Sounds like you won't be going any where with this girl. Wait until she is living on her own and not so dependent on her parents before you try to "take things to the next level" with her. If you can't wait that long, then she's not the one for you and you should look elsewhere.

As to dating friends. Yes, if things don't work out, it can be awkward, especially if things ended badly. You can go back to being friends if things ended well, but you may still need some time apart before the friendship can be renewed. You will have to weigh the merits and disadvantages of starting a romantic relationship with a friend and decide for yourself if the risks are worth it.

Personally, I think that it's better to try and fail than to always wonder. but that's me.

Welcome to adulthood and Good Luck!

edit: if she's still living in her mother's home, then the "my house, my rules" mentality is valid to a point. But the "my house, my rules" should only involve things like: mom's house and mom's money. So she can't have sleep over dates, she can't throw parties in the house. And if mom is paying for the daughter's lifestyle, then that gives mom SOME (not ALL) say in what daughter can buy and not buy with that money. But that shouldn't be that daughter can't date. If that is the case and daughter wants to date, then daughter needs to move out.

so I still stand by the statement: You may have to wait until daughter is no longer dependent on mom.

BTW: are you sure that is the truth or is it just her excuse?