My best friend's sister

[SuperShyGuy]

My best friend's sister just turned 18 and I am very interested in her. She is intelligent, funny, and a whole lot prettier than she gives herself credit for. I'm only 21 so I don't think I'm being a creep or anything. I want to approach her but I also don't want to make too much noise about it.

My friend wouldn't mind, but I think her parents might. To be honest, I'm not to sure about how she would react to it either. I don't want to risk having this whole thing blow up in my face.

Should I try to start up more than just a casual friendship with this girl or should I just try to put the whole thing out of my mind? If anyone thinks I should try this any good suggestions about doing it descretly?

 

[DuckLover]

I think one definite factor is your current relationship with her. Do you two talk casually? Or are you friends?

If you have a pretty good relationship, even platonically, then simply asking her out for coffee or something is unlikely to blow up in your face. If your really nervous, try just inviting her to go along with you, her bro, and some others on a group event. ("Hey Kim, we're all going to the movies and then for dessert. Wanna come along?")

Good luck!

 

[paintergrl]

This is a really tricky situation. I suggest talking to her, causally, and to your friend about this. I have been on the other side of this situation. My best friends older brother is interested in me, and the way he went about it really made me uncomfortable. I'm sure I would have been more open to the idea if I knew how he felt. He tried to be my friend, and then take it to another level at the same time. So just take your time about the whole thing, either be her friend, or something more. Just kind of ask her out, go to casual places, treat her like any other girl that you are interested in. But keep your friend in mind. Good Luck, Hope this helped.

 

[fgarvb1]

If i was in your place i would test the waters first, so to speak.

If she is interested and given the chance, most of the time they will let you know.
I'm not saying you should not or can't enhance your chances by legal and socially accepted means.

Just remember she is only eighteen.

 

[peachykeen]

I think one definite factor is your current relationship with her. Do you two talk casually? Or are you friends?

If you have a pretty good relationship, even platonically, then simply asking her out for coffee or something is unlikely to blow up in your face. If your really nervous, try just inviting her to go along with you, her bro, and some others on a group event. ("Hey Kim, we're all going to the movies and then for dessert. Wanna come along?")

Good luck!

This is very good advice.

 

[StaceyR]

Well since I'm 18, I don't think that you'd be a creep for approaching her..I certainly wouldn't have a problem with it, especially since you seem like you're truly interested in her instead of the way some guys around your age think they can get a quick lay out of younger girls. If you find out that she's interested in you, go for it and don't worry about it, three years is not a big deal. As far as her parents go...if she's your best friends sister shouldn't they know you enough to realize that you aren't just trying to take advantage of her?

 

[SuperShyGuy]

As far as her parents go...if she's your best friends sister shouldn't they know you enough to realize that you aren't just trying to take advantage of her?

Well you know the old cliche about "daddy's little girl"? Her dad knows me pretty well but I still get the impression that if I tried to start up anything it could get a bit uncomfortable. I'm certanly not saying that I'm just trying to get her in bed, because I'm not. I'm just saying if we ever did become intimate it could get pretty awkward. It's not that I don't have any self control or something, it's just that when you put a 21 and and 18 year old in the same room, common sense doesn't always abound.

I've always been to shy to ask girls out like a normal bloke so I was thinking about maybe writing my feelings for her and sending that to her, a good old fashioned "love letter". Well, maybe love letter is a little to strong a wording but you get the idea. Ladies, if someone approached you in this way would it come off as to hokey or would it interest you? Of course this assumes you have some interest in the sender of such a letter. I would love to hear some feedback on this.

 

[SuperShyGuy]

bump

 

[SuperShyGuy]

bump

 

[SuperShyGuy]

bump

 

[StaceyR]

your bumping doesn't seem to be working..

 

[Madame Manga]

A love letter first? Whoa, cowboy. That's putting the cart before the horse. Talk to the lady--if you have to write it out ahead of time and crib it, do so, but don't pour it all out at her feet yet. You don't know if she's just going to wipe it off her shoe.

You are very liable to spook her if you come on too strong all at once. I know--I was spooked more than once at that age by earnest young men who wore their hearts too conspicuously on their sleeves. I have in mind one guy who on the basis of a casual get-acquainted conversation about science fiction hand-wrote a twelve-page list of all the science fiction novels in his library with capsule reviews and recommendations. It arrived in the mail a few days after I met him for the first time. Can you see me sprinting in the opposite direction? He kissed himself goodbye with a great deal of time and effort expended.

Just give her some hints that you like her to get her mind going in that direction. Plant little seeds and be patient while waiting for them to sprout. Be a nice guy, be available some of the time, but don't wait under her window with a guitar and jump at every opportunity. Too eager is much, much worse than a little calculated bait and switch. Make yourself into at least a little bit of a challenge, or you look too easy (and too desperate). Does that sound like a game? Not really--it's feminine psychology in action. 'Not too much noise' is definitely the way to go.

MM