How do I ask out my best friend? First date advice please?

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Anonymous #1
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Follow up from my previous post (http://www.thestudentroom.co.uk/show....php?t=3830639)

Tl;dr - I started to feel like the relationship between me and my best friend of 6 years might potentially become something more. She's someone I really like a lot, we're super in tune with each other/exact same sense of humor, very compatible, people always say we're basically the same person when we're together. I like her a lot and am definitely interested in pursuing a romantic relationship with her if she feels the same way. I'm obviously paranoid of ruining our friendship in anyway or creating awkwardness because first and foremost she's my best friend so I really want to tread on this lightly in case theres a chance she doesn't return the feelings.

I got some helpful advice in my last post, people encouraging me to ask her out or just outright ask her if she has any romantic feelings. I'm now planning on asking her out and subtly bring up the idea but the question is how? I'm a bit of a shy guy and would really appreciate any tips on how to bring it up/ask her in a way that is subtle and not too "in your face" or forward in an off putting way. We've never been romantic in anyway so this is completely new territory as far as our relationship goes.

Also what would be a good idea for a first date assuming she does say yes? Bear in mind we've known each other for quite a bit so it's not a first date with a stranger?
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Anonymous #1
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UWS
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Are you sure she likes you back? You need to be sure before you ask such a close friend out. So because of this I would really think about it if I were you. Don't just rush to a decision because you like her.

She's your best friend so you need to be careful. You are right in speculating that the friendship could well be awkward if she says no. But that is the risk you are taking and if you're willing to take it then I can't stop you. But just speaking from personal experience, it didn't go down well when I asked my good friend out. Reading other threads on here, it hasn't gone too well for others too.

If your mind is already set I would just ask her out normally to be honest. If you try to beat around the bush and not be too direct, she's going to think you're joking or think it's a casual meet up. So tell her how you feel, ask her out and then see what happens. But think about it first.
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Anonymous #1
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(Original post by UWS)
Are you sure she likes you back? You need to be sure before you ask such a close friend out. So because of this I would really think about it if I were you. Don't just rush to a decision because you like her.

She's your best friend so you need to be careful. You are right in speculating that the friendship could well be awkward if she says no. But that is the risk you are taking and if you're willing to take it then I can't stop you. But just speaking from personal experience, it didn't go down well when I asked my good friend out. Reading other threads on here, it hasn't gone too well for others too.

If your mind is already set I would just ask her out normally to be honest. If you try to beat around the bush and not be too direct, she's going to think you're joking or think it's a casual meet up. So tell her how you feel, ask her out and then see what happens. But think about it first.
Hi, UWS thanks a lot for your reply and advice
The truth is i'm not sure if she likes me back. You're right, I really am thinking very carefully about how to proceed in the situation. Do you might telling me exactly what happened with your friend if its not too personal?

I guess I just don't know. I don't know if i'm in over my head or if there's something actually there. I do want to believe that theres a potential for something more, but there's no way for me to be sure if the signs are real or just a result of my own desires(?) I definitely don't think its a good idea to outright ask her anymore, i wont risk our friendship that way.

I'v been thinking a good way might be to just test the waters a bit i guess?
Like being very subtle with flirting, little hints, basically just very subtle things that might make her see a potential with me as a romantic partner/more than a friend if she doesnt already. That way I guess I can see how she responds and it should be subtle enough that I can gauge her response without risking awkwardness if the feelings arent reciprocated. and if i get what seems to be a positive response then i can outright ask her out... but not until I feel very certain that there might be something.

so i guess now i'm just trying to figure how to be subtle etc
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UWS
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(Original post by Anonymous)
Hi, UWS thanks a lot for your reply and advice
The truth is i'm not sure if she likes me back. You're right, I really am thinking very carefully about how to proceed in the situation. Do you might telling me exactly what happened with your friend if its not too personal?

I guess I just don't know. I don't know if i'm in over my head or if there's something actually there. I do want to believe that theres a potential for something more, but there's no way for me to be sure if the signs are real or just a result of my own desires(?) I definitely don't think its a good idea to outright ask her anymore, i wont risk our friendship that way.

I'v been thinking a good way might be to just test the waters a bit i guess?
Like being very subtle with flirting, little hints, basically just very subtle things that might make her see a potential with me as a romantic partner/more than a friend if she doesnt already. That way I guess I can see how she responds and it should be subtle enough that I can gauge her response without risking awkwardness if the feelings arent reciprocated. and if i get what seems to be a positive response then i can outright ask her out... but not until I feel very certain that there might be something.

so i guess now i'm just trying to figure how to be subtle etc
Well what happened in my case is I let my emotions get the better of me. One of my closest friends at the time was being very friendly to me. I misread the signs and thought it was her being interested in me but I screwed up. She said no. We never talked again since and that was 2 years ago. I lost a good friend because I didn't think about the consequences. I would have tested the waters, though I was 50:50 on the matter. I was getting mixed signals but I risked the friendship anyway and paid the ultimate price.

People will tell you to just go ahead and do it, but they've never been in that situation before. I'm speaking from first hand experience and it'll hurt you if she says no. Of course there is that chance she will say yes, but when you're dealing with a close friend, especially with a best friend then you really need to proceed with caution. If she says no then there are 3 possible outcomes:

1) She may not want to talk to you again as to prevent giving you false hope in the future, therefore you lose a friend.
2) You stay friends but you may not be able to mentally cope with being 'just friends', thus you could lose her too.
3) You stay friends and things go back to normal. You'll still have feelings for her but you can deal with it over time.

I've learned from my mistake now. I'd only ask one of my close friends out if I'm 100% sure that she likes me. Normally with close friends, they'll act more friendly to you and it's easy to misinterpret it as a sign of interest.

So good luck. I would just test the waters, perhaps put your arm round her when you're together or just touch her arm and see her reaction. If she pulls away or gives you a confused look then it's time to abandon ship and avoid asking her out.
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Conkerr
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UWS sent me the link of this thread because I was in the same situation very recently.

The girl was one of my best friends at the time. I was almost sure she wasn't interested in me, but I just had to tell her. I wasn't even expecting a positive answer, I just wanted her to know. One night we went out, she got really (too) close to a guy and on the way home at 6am, I just told her. I thought that I had to try. Of course she rejected me. She basically said she had already been through what I was going through so she knew it was hard for me but she just didn't have feelings for me. I was one of her best friends and she wanted things to stay the same.

That was about 1 month ago. We're still good friends but we've had about 2 or 3 serious arguments since then (we had never had one before). I feel like I can tell her everything after that and she is easily offended so... It doesn't often end well. She didn't really change, she's still very comfortable around me. It's still hard for me. It's really hard to be around the girl you like, especially if she's not shy with guys if you see what I mean... But that's my only solution because I don't want to lose her and we have a lot of mutual friends so I want to avoid her I'll have to stop hanging out with them too.

I've been there but I don't know what to tell you to be honest. If you don't think you have a good chance she will say yes just don't bother telling her. Because there is a possibility things will never be the same anymore between you. If you tell her, she says no but she's understanding and you're ready to make efforts to keep her as a friend and forget your feelings, you'll be able to stay friends. You should probably test her and see how she reacts.
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Anonymous #2
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I agree with the others that this isn't worth pursuing if you don't have a good expectation of a "yes". In general, if a girl isn't giving you any hints, then she probably doesn't like you in that way.

You're more likely to be successful if you can start flirting - joking, gentle "insults", then occasional touching, etc. That way you'll be able to escalate things if she responds. You might also make her begin to think about you in that way and, in which case, she'll think she's initiating things and you are in the power seat. If she doesn't respond then there's your answer.
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Anonymous #1
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(Original post by UWS)
Well what happened in my case is I let my emotions get the better of me. One of my closest friends at the time was being very friendly to me. I misread the signs and thought it was her being interested in me but I screwed up. She said no. We never talked again since and that was 2 years ago. I lost a good friend because I didn't think about the consequences. I would have tested the waters, though I was 50:50 on the matter. I was getting mixed signals but I risked the friendship anyway and paid the ultimate price.

People will tell you to just go ahead and do it, but they've never been in that situation before. I'm speaking from first hand experience and it'll hurt you if she says no. Of course there is that chance she will say yes, but when you're dealing with a close friend, especially with a best friend then you really need to proceed with caution. If she says no then there are 3 possible outcomes:

1) She may not want to talk to you again as to prevent giving you false hope in the future, therefore you lose a friend.
2) You stay friends but you may not be able to mentally cope with being 'just friends', thus you could lose her too.
3) You stay friends and things go back to normal. You'll still have feelings for her but you can deal with it over time.

I've learned from my mistake now. I'd only ask one of my close friends out if I'm 100% sure that she likes me. Normally with close friends, they'll act more friendly to you and it's easy to misinterpret it as a sign of interest.

So good luck. I would just test the waters, perhaps put your arm round her when you're together or just touch her arm and see her reaction. If she pulls away or gives you a confused look then it's time to abandon ship and avoid asking her out.
Thanks so much UWS for telling me about your experience and all the helpful advice, i really appreciate you taking out of your time to help me with this.
I agree with a lot of what you said and really dont want to risk our friendship here, but I guess I'v also been thinking "shouldnt I just find out once and for all if anything's there?" for closure if anything else.

The thing I should stress is that i'm not in love with her, i dont have deep romantic feelings or anything like that. I'm not going to be heartbroken or crushed if she says no. for me those are the sorts of feelings that develop over time being with someone. Right now what i feel is that there's a 'spark', and a knowledge that those feelings could develop into something more if she feels the same. For me personally its impossible to have strong feelings like that for her when we've never been romntically involved, i'v only known her as a friend and therefore have no idea what being together as romantic partners would be like. its something i would love to find out and i'm definitely interested in pursuing a romantic relationship if she feels the same way/seeing if something develops but that interest only exists if the feeling is mutual and thats why i want to find out so badly.

I think it might be worth it to just clear the air and get it out of the way in a lighthearted way that isnt uncomfortable or awkward. something simple during a conversation "hey, so i'v been wanting to ask, i'v been wondering if you'd like to go out sometime with me? On a real date. Totally cool if not honestly, no awkwardness, just wondering." and laugh it off. that way she knows that its not a big deal if she says no and there wont be hard feelings and things can just go back to normal.

The thing about me is that I only feel romantic attraction to people who return/have the potential to return those feelings. Once I know she's not interested in being more than friends then i'll be totally fine going back to normal! I was telling myself i would try to start subtle; light flirting, very subtle hints to test the waters but now I dont think its a good idea, i think thats even worse than just being direct because it just feels unwarranted, might make her uncomfortable if she doesnt know why and is more likely to negatively affect our friendship than just outright asking if she might want to go on a romantic date and see where it leads. if not, cool we can still be best buddies and everything will be as it were.

So hopefully she'll yes and will be interested in testing the waters, but if she says no i know at least from my end there wont be any awkwardness or hard feelings, i'm just worried about making her feel awkward or think that i'm in love with her or something which might make her not trust our friendship. thats my biggest concern, so i need to find a way to make sure she understands that its not the case.

Thanks so much for all the help! you've really helped me think this through much better than i did before
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Anonymous #1
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(Original post by Anonymous)
I agree with the others that this isn't worth pursuing if you don't have a good expectation of a "yes". In general, if a girl isn't giving you any hints, then she probably doesn't like you in that way.

You're more likely to be successful if you can start flirting - joking, gentle "insults", then occasional touching, etc. That way you'll be able to escalate things if she responds. You might also make her begin to think about you in that way and, in which case, she'll think she's initiating things and you are in the power seat. If she doesn't respond then there's your answer.
I think there may have been hints, but in this situation its just very hard to be sure you know? Thats the only reason I even started to feel this way because I felt like there was a genuine potential, but i know completely that I could be wrong. I was telling myself i would try to start subtle; light flirting, very subtle hints to test the waters but now I dont think its a good idea, i think thats even worse than just being direct because it just feels unwarranted, might make her uncomfortable if she doesnt know why and is more likely to negatively affect our friendship than just outright asking if she might want to go on a romantic date and see where it leads, and make it very clear to her that i'm her friend first and foremost and theres no hard feelings if she says no, nothing will change from my end at least.
Hopefully she does consider me in that way *fingers crossed* but i wont know til I ask
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