Telling Her I Like Her....A Lot.

[Rembrandt500]

Sort of a juvenile question but I feel a lot of people have been there at some point and any advice would be appreciated very much.

So, there's this female friend of mine who I've known for about 2 years now. She's my good friend's sister, and she's just incredible. She's sweet, she's very intelligent, she's artistically creative, and she's just so incredibly beautiful. Lately (over the past 8 months) we've been becoming even better friends after having dinner at her family's house a few times, working on artsy projects together, etc. and each time I see her, I seem to like her more and more.

A few months ago, I managed to buck up and I asked if she wanted to go out to this party with me, and she said it was sweet of me to ask, but it might be awkward because I'm her brother's friend. I said it was cool and I apologized if I put her on the spot, and she said not at all, and that she wasn't planning on going with anyone anyway. Thankfully, we've been able to still talk and hang out as if nothing happened and it's not awkward or anything.

The downside is that she DID attend the party with this big, buff dude who would later become her boyfriend, and later she would often tell me what an ass he is and how their relationship has no substance. I wanted so badly to tell her how happy I wanted to make her, how much she truly meant to me, but I didn't want to take another chance of ruining our friendship, so I kept my silence.

So apparently she and this dude broke up, and she and I are in the middle of working on a project together, and we're also going to be hanging out next week with some mutual friends of ours. All I've been thinking about lately is how badly I want to tell her how I feel about her, not that I just think she's cute or whatever, but that she's one of the most incredible people I've ever met and I want to give us a shot. If she tells me she's just not into me that way, I'd be TOTALLY cool with that....granted, it'll suck, but I'd be fine with it, but the reason (supposedly) she turned me down was because it would be awkward given my friendship with her brother. I understand it might be a bit awkward at first (he doesn't know I like her), but it doesn't matter. I just want to tell her how I feel, with some semblance of tact and without putting her on the spot.

So....should I tell her? Should I not? If I should, what would be a good way to do so? Does it seem from what I've mentioned that she's not attracted to me?

 

[_Virginia_]

I think that if she was attracted to you, she would have accepted your invitation to go to that party. Telling her that you 'like her a lot' would probably make things pretty awkward. Probably not what you wanted to hear, but it doesn't sound like she wants anything but friendship.

 

[DuckLover]

Tough situation

That's a tough situation, and one that I'm sure all of us have been in, in one form or another. Particularly given how strongly it sounds like you feel, I say YES, absolutely you should tell her. If for no other reason, then you'll likely be miserable and second-guessing yourself for as long as you interact with her if you don't.

Now, she may say no, she's not interested. The "awkward with her brother" angle could just be a convenient out. If you want to short-circuit that one, casually raise the topic with him. Maybe mention that with all the time you and she hung out, you've realized just how cool she is and how much you have in common. Then maybe try something like, "Heck, I've even thought of asking her out!" See how he responds. If he's pissed, you could play it off as a joke, but it's likely he'll just shrug.

When you talk to HER, consider a similar approach - pointing out that with all the time you spend together, you've really come to appreciate how great she is and how much you have in common. Mention a couple specific things you admire about her and that are common interests. (Don't use her looks as one of them.) Then ask if she'd like to go out, ideally offering a concrete day/time/activity. I'd avoid something like a party where you'll both be socializing widely; pick something where you'll be interacting with each other. Unless you're in high school, that also means no movies - sitting silently next to each other focusing on the screen is a pretty lame date. Try something based on those mutual interests. Is there an art opening nearby? A short workshop you could take together? A local landmark to check out? Picnic? The classic "drinks after work"?

Good luck!

 

[SweetErika]

I think you pretty much already told her by asking her to the party and via other signals. She declined then, and if her brother is an issue, it's still there, so you're probably going to be stuck in the friendship zone. I'd also imagine if she felt the same about you and her brother was the main barrier, she would have talked to him (or asked you to get his blessing first).

Are you close enough to her brother that you could get his advice on the situation, or would that be a bad idea?

 

[fire_breeze]

Sort of a juvenile question but I feel a lot of people have been there at some point and any advice would be appreciated very much.

So, there's this female friend of mine who I've known for about 2 years now. She's my good friend's sister, and she's just incredible. She's sweet, she's very intelligent, she's artistically creative, and she's just so incredibly beautiful. Lately (over the past 8 months) we've been becoming even better friends after having dinner at her family's house a few times, working on artsy projects together, etc. and each time I see her, I seem to like her more and more.

A few months ago, I managed to buck up and I asked if she wanted to go out to this party with me, and she said it was sweet of me to ask, but it might be awkward because I'm her brother's friend. I said it was cool and I apologized if I put her on the spot, and she said not at all, and that she wasn't planning on going with anyone anyway. Thankfully, we've been able to still talk and hang out as if nothing happened and it's not awkward or anything.

The downside is that she DID attend the party with this big, buff dude who would later become her boyfriend, and later she would often tell me what an ass he is and how their relationship has no substance. I wanted so badly to tell her how happy I wanted to make her, how much she truly meant to me, but I didn't want to take another chance of ruining our friendship, so I kept my silence.

So apparently she and this dude broke up, and she and I are in the middle of working on a project together, and we're also going to be hanging out next week with some mutual friends of ours. All I've been thinking about lately is how badly I want to tell her how I feel about her, not that I just think she's cute or whatever, but that she's one of the most incredible people I've ever met and I want to give us a shot. If she tells me she's just not into me that way, I'd be TOTALLY cool with that....granted, it'll suck, but I'd be fine with it, but the reason (supposedly) she turned me down was because it would be awkward given my friendship with her brother. I understand it might be a bit awkward at first (he doesn't know I like her), but it doesn't matter. I just want to tell her how I feel, with some semblance of tact and without putting her on the spot.

So....should I tell her? Should I not? If I should, what would be a good way to do so? Does it seem from what I've mentioned that she's not attracted to me?

You poor thing.

I used to be/am that girl. My brother and I are extremely close - we're not just siblings but actually very good friends - with a mutual group of friends. I don't think I've ever thought of any of our mutual guy friends "that way". Also, if I did date any of those guys, I might feel awkward around my brother. After all, I'm sure that my brother does not need to know the details, nor do I exactly want to know that the guy I'm dating will be telling him that.

Add to the fact that my brother is ridiculously protective of me (as in, he in put a moratorium on my dating life until after I've settled down. Granted, the last guy before this one broke my heart something awful). Anyway, combined made me think twice before I'd get involved with any of our mutual friends, so if one of them does ask me out, I would be hesitant. Not that it will be a problem, as I gushed to brother dearest about the one I completely adore, so I think he may have relented a bit, but I digress.

That said, I don't know the relationship between the girl that you like and her brother. They may be close, they may not. He may be protective of her, he might not give a shit. What I do suggest is to tread carefully - if you like her and want her to know, then tell her but be cool about it. Let her know but don't push the issue. And by the way, tell HER and not her brother first. Trust me.

Good luck.

 

[Rembrandt500]

That said, I don't know the relationship between the girl that you like and her brother. They may be close, they may not. He may be protective of her, he might not give a shit.

They're kinda close, but they do have their arguments. Just the other day, they got into a pretty big argument about something really small around the house, and he tells me she kind of annoys him sometimes. He's kind of protective of her but not extremely noticeably.

What I do suggest is to tread carefully - if you like her and want her to know, then tell her but be cool about it. Let her know but don't push the issue. And by the way, tell HER and not her brother first. Trust me.

Good luck.

Thanks a bunch.

And thanks for all your comments so far, people. This has been really stressful lately and I'm just so lost as to what to do. Common sense is telling me to move on, but everything else is saying, "Make a move!" I feel like a schmuck for having these feelings towards her and I wish I wasn't attracted to her at all so this would be so much easier on me. It sucks so badly liking the "wrong" people (aka the ones who probably don't like you back), but hey, that's a fact of life, I guess.

 

[Patchouli]

Do you like her so much that you'd be willing to possibly ruin your friendship to date her? If you come straight out and tell her you like her, that's very much what might happen.

you're in a tricky situation. On the one hand, a lot of girls might wait for you to make a move on them. On the other, and this is the important one, generally speaking, if two people like each other, it happens with very little prompting on either side. You may need to just accept that she's not into you and move on. If you can't accept that, then you need to just make a move. Don't torture yourself forever over this.

Whatever you do, if you really like her, don't let her treat you like a faux boyfriend. That really hurts and will eventually make you hate her. It would be better to take a little break and get your head on straight then to let her keep stringing you along, which is kinda what it sounds like she's doing.

Anyway, I really hope you get through this unscathed. It's rough, and I'm sure we've all been there. Just remember that you deserve your own respect, and remember to act like it. I really do feel for you.

 

[NippleMuncher]

Several scenarios and consequences for you.

1 - Leave things as they are between you, remain friends and get to interact and enjoy each others company (including friendship with her brother).
2 - Lay it out for her - tactfully - that you very much enjoy her company and would like to pursue a more intimate relationship with her. She will either accept your offer to become more than friends and all will be good or she will decline your offer and things will likely be awkward from that point forward IF you can continue a relationship at all, which in turn will affect your friendship with the brother. If you go this route, be certain that you are ok with either outcome.
3 - You begin a relationship with her - will it be awkward to still hang out with the brother? Will it be awkward to not include her when doing things with the brother? If the relationship goes bad, you will likely lose both her AND her brothers friendship.

 

[Nasty_Deeds]

Sort of a juvenile question but I feel a lot of people have been there at some point and any advice would be appreciated very much.

So, there's this female friend of mine who I've known for about 2 years now. She's my good friend's sister, and she's just incredible. She's sweet, she's very intelligent, she's artistically creative, and she's just so incredibly beautiful. Lately (over the past 8 months) we've been becoming even better friends after having dinner at her family's house a few times, working on artsy projects together, etc. and each time I see her, I seem to like her more and more.

A few months ago, I managed to buck up and I asked if she wanted to go out to this party with me, and she said it was sweet of me to ask, but it might be awkward because I'm her brother's friend. I said it was cool and I apologized if I put her on the spot, and she said not at all, and that she wasn't planning on going with anyone anyway. Thankfully, we've been able to still talk and hang out as if nothing happened and it's not awkward or anything.

The downside is that she DID attend the party with this big, buff dude who would later become her boyfriend, and later she would often tell me what an ass he is and how their relationship has no substance. I wanted so badly to tell her how happy I wanted to make her, how much she truly meant to me, but I didn't want to take another chance of ruining our friendship, so I kept my silence.

So apparently she and this dude broke up, and she and I are in the middle of working on a project together, and we're also going to be hanging out next week with some mutual friends of ours. All I've been thinking about lately is how badly I want to tell her how I feel about her, not that I just think she's cute or whatever, but that she's one of the most incredible people I've ever met and I want to give us a shot. If she tells me she's just not into me that way, I'd be TOTALLY cool with that....granted, it'll suck, but I'd be fine with it, but the reason (supposedly) she turned me down was because it would be awkward given my friendship with her brother. I understand it might be a bit awkward at first (he doesn't know I like her), but it doesn't matter. I just want to tell her how I feel, with some semblance of tact and without putting her on the spot.

So....should I tell her? Should I not? If I should, what would be a good way to do so? Does it seem from what I've mentioned that she's not attracted to me?

Why don't you just tell her that you want to date her? She is never going to take you serious if you keep beating around the bush. (no pun intended)

 

[Rembrandt500]

Why don't you just tell her that you want to date her? She is never going to take you serious if you keep beating around the bush. (no pun intended)

It's not really that easy. Typical excuse I know.

The reason I haven't said that yet is because of the very high possibility that she will not only say no, but that it may also be very awkward between us, which will suck.

But you know what? I've made up my mind - I'm going to tell her. Tactfully of course, and in the proper setting.

Oh, but did I mention my other problem: I'm cripplingly socially awkward when it comes to women. I have little to no clue how to word it except something like:

"I'm really glad we've have become good friends, but after hanging out with you and talking to you more, I've started to like you a lot. You have this really bubbly personality, you're sweet and you have such unique creativity (I'll probably re-word this). And I was wondering if you'd go out with me sometime. If you need to think about it, take your time."

 

[sphy2]

Judging over the internet, from your writing, I would imagine that telling her how you feel right now will lead to rejection. Which is fine, it will help you get over her faster.

But if you reaaaaally want to date her, the best advice is always to be yourself (it's not worth it to be in a relationship where the other person expects you to behave in a way that is not your true nature) and to be confident. If you're not feeling confident right now then wait until you can be in that mindset. Be comfortable with your personality/strengths/weaknesses and she will see you for what you are. It might not work out with this girl, but learning to be confident in yourself will pay off in the long run.

and bathe. with soap. no one wants to date a stinky person.

Figure out something she definitely would like to do and then offer to take her, perhaps go as a group and casually, like it's no big deal. At this point you're just exploring a possibility and it's clear she has put up some walls. Work to disarm her reservations and leave out the 'feelings' part until it's clear that she is in a similar place or she won't be receptive.

It still might not work, but I think that's your best shot.

 

[Nasty_Deeds]

It's not really that easy. Typical excuse I know.

The reason I haven't said that yet is because of the very high possibility that she will not only say no, but that it may also be very awkward between us, which will suck.

But you know what? I've made up my mind - I'm going to tell her. Tactfully of course, and in the proper setting.

Oh, but did I mention my other problem: I'm cripplingly socially awkward when it comes to women. I have little to no clue how to word it except something like:

"I'm really glad we've have become good friends, and after hanging out with you and talking to you more, I've started to like you a lot. You have this really bubbly personality, you're sweet and you have such unique creativity (I'll probably re-word this). And I was wondering if you'd go out with me sometime. If you need to think about it, take your time."

Glad you decided to tell her. She will either say yes or no, and whatever her answer, she isn't going to stop being your friend just because you have shown an interest in dating. As far as being awkward, it's awkward now. Sometimes the direct approach is best. At least you will know where you stand with her.

 

[subwannabe]

I'm surprised no one has suggested what came into my mind. Ditto your last session. Don't go overboard telling her your feelings but say the same exact thing you said the first time, the same exact way. If she turns you down you can still be friends and then you will know to never ask her again. If she says yes then you can take it from there. Oh, by the way, don't ask her to a party, just say something like that you like her and was wondering if she would like to have lunch sometime. Make it a date that can be kind of construed as not really a date. If it goes well then I think I would ask her how she felt about going on a real date sometime.

 

[Felix_Jones]

Yeah, this isn't a romantic comedy dude. When you declare your feelings she'll blush, stammer and then want to crawl into the deepest darkest hiding place she can find. It will be awkward, time to move on.

 

[SweetErika]

It's not really that easy. Typical excuse I know.

The reason I haven't said that yet is because of the very high possibility that she will not only say no, but that it may also be very awkward between us, which will suck.

But you know what? I've made up my mind - I'm going to tell her. Tactfully of course, and in the proper setting.

Oh, but did I mention my other problem: I'm cripplingly socially awkward when it comes to women. I have little to no clue how to word it except something like:

"I'm really glad we've have become good friends, but after hanging out with you and talking to you more, I've started to like you a lot. You have this really bubbly personality, you're sweet and you have such unique creativity (I'll probably re-word this). And I was wondering if you'd go out with me sometime. If you need to think about it, take your time."

I think that would make nearly any girl feel uncomfortable. If you're determined to do this, you've got to muster up the necessary confidence and ease. Invite her to something you'll both really enjoy. If she accepts, go have fun and see if there's chemistry on her part. If she declines, let it go and find someone who's interested in you romantically.

 

[Rembrandt500]

Yeah, remember the bit where I said I was phenomenally socially awkward? My little failure of a paragraph above just proved it. I'm seriously bad at this, people lol

Yeah I'll just casually ask her to an event we both enjoy and I won't make a spectacle of it.

 

[tenderlily]

Yeah I'll just casually ask her to an event we both enjoy and I won't make a spectacle of it.

That sounds like a much better approach . It's always awkward when you have a crush on someone. Hell I can be pretty awkward just in general situations.

Good luck and let us know how it goes.

 

[NippleMuncher]

Oh, by the way, don't ask her to a party, just say something like that you like her and was wondering if she would like to have lunch sometime. Make it a date that can be kind of construed as not really a date. If it goes well then I think I would ask her how she felt about going on a real date sometime.

I agree completely with this. I would ask her to coffee or lunch, but do it in a manner that you're not "asking" her on a date. Something along the lines of:

- You've been wanting to trying that new coffee house/restaurant/burger house, would she like to join you?

- You're going to be in her neighborhood/near her place of work on such and such a day running errands, wanna grab some lunch or coffee?

- You're heading to the park, going for a bike ride, to the local museum, etc., would she like to tag along?

To express things in this manner, you're saying that you're already going to do these things on your own, but would enjoy her company if she's free.

 

[Rembrandt500]

Minor update - her friends dropped out for Sunday, that day we were all supposed to hang out, but they said they would reschedule for another day. She said she might still go that day without them and she'd let me know if she did, so we MAY be hanging out alone I promise not to act out of the ordinary when/if we do, although I am going to ask if she wants to go to this local event at the park, sort of an exhibit/concert thing, and I'll let you guys know what happens.

 

[subwannabe]

Best of luck. Sounds like maybe she was dropping a very subtle hint to you. Maybe she's been asking her friends for advice on how to approach you after she had already turned you down.

 

[Patchouli]

Good luck, rembrandt.

 

[Patchouli]

Strangely, I'm finding my mind wandering to you and your situation. I know today is the day that you're supposed to hang out with her. I wished you luck before, but I really hope that things are going well.

 

[Rembrandt500]

Thanks, Patchouli, and everyone! Alright, so here's what happened:

We planned on going to the arcade with her friend and possibly my friend, but she said she wanted to go shopping for possible costumes for this short film we're working on, so we met up there first. That went pretty well, although I'm not sure if she just viewed me as a "safe" friend or as anything more, you know? She did joke around with me once or twice, saying, "I'm gonna teach you how to shop with a woman - it's a skill every guy has to have." So that went alright but when we went to the arcade, it was closed, luckily her friend didn't show up yet. So we just went our separate ways. Oh also I asked if she wanted to go to the exhibit but she said she had to work that day. We're gonna be in communication this week regarding film preparation though, mostly over the internet and texting, unless I can make up an excuse to talk about it over lunch or something.

 

[Nasty_Deeds]

Thanks, Patchouli, and everyone! Alright, so here's what happened:

We planned on going to the arcade with her friend and possibly my friend, but she said she wanted to go shopping for possible costumes for this short film we're working on, so we met up there first. That went pretty well, although I'm not sure if she just viewed me as a "safe" friend or as anything more, you know? She did joke around with me once or twice, saying, "I'm gonna teach you how to shop with a woman - it's a skill every guy has to have." So that went alright but when we went to the arcade, it was closed, luckily her friend didn't show up yet. So we just went our separate ways. Oh also I asked if she wanted to go to the exhibit but she said she had to work that day. We're gonna be in communication this week regarding film preparation though, mostly over the internet and texting, unless I can make up an excuse to talk about it over lunch or something.

It sounds like you two are just friends, and it's not likely going to be anything more. It least from her viewpoint.

 

[Rembrandt500]

Okay.

Maybe I do need to get over her, but to be honest I'm just getting extremely tired of having to train myself not to like women who don't like me back. I understand that's the way it is, life's not fair and blah blah blah, but it's just really fucking hard.

I don't mean to be a downer, I'm just venting.