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Want to make a move with this girl on Valentines day... but don't want to scare her off. Any tips?

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Question - (7 February 2007) 4 Answers - (Newest, 28 February 2007)
A male United Kingdom age 51-59, *obo writes:

I'm a thirtysomething man who's not had a real gf other than short term (mostly drunken) 'encounters'. We have a group of friends that have been hanging out for a few years now, the men the same age as me, the ladies in their early twenties (my best friend married one of their group). Recently I've come to realise that I'd like to be more than friends with one of the girls. The problem is she keeps her feelings to herself and is quite private and I'm not sure how she feels about me.

With Valentines day coming up I'd like to do something but am terrified about what could happen. First off I don't want to frighten her off and lose her as a friend. Secondly, I've never been the one to make the first move so far and am not sure where to start. Do I get her some flowers anonymously then confess all later? Any other ideas?

View related questions: best friend, drunk, flowers

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A male reader, lobo United Kingdom +, writes (28 February 2007):

lobo is verified as being by the original poster of the question

I suppose it's time for an update............... Our mutual friends persuaded me to wait until after St Valentine's day as we were going to a concert together soon after and I didn't want her to miss it. Had an absolutely fantastic night and were on a high as we left the gig. So much so that she pulled out her mobile to tell her new boyfriend all about it.

Words can't really express what I felt at that moment but didn't feel too bad. Must have been the gig as since then I've been absolutely devastated, at least I know how I really feel about her now. Hopefully time will be a healer and I'm going to keep away for a few weeks if I can (not easy as we tend to hang out as a group). Things are getting better but only time will tell.

Sorry to end the story on a downer but thanks for your advice.

All the best

Lobo

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A female reader, AskEve United Kingdom +, writes (9 February 2007):

AskEve agony auntI'll keep my fingers crossed for you. Let me know how it goes okay? ;o)

Eve

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A male reader, lobo United Kingdom +, writes (9 February 2007):

lobo is verified as being by the original poster of the question

Thanks for the tips Eve. Since posting I've been in touch with one of her friends and she's going to quiz her over the next day or so. At least I can avoid upsetting her that way. Finger crossed, if I hear back soon I can start making plans. OMG this is beginning to sound like a military operation ;o)

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A female reader, AskEve United Kingdom +, writes (8 February 2007):

AskEve agony auntWhy don't you tell her you really enjoy hanging out with her and does she fancy going for dinner with you one night? Then make it valentine's night? I'm sure she'd jump at the chance. Once out with her just be yourself but go easy on the alcohol so you don't make a fool of yourself.

Make a real effort and dress smart and smell good. If she likes you then she certainly won't refuse. It may be she's genuinely busy that night, if so, then give an alternative night or ask her what night suits.

Good luck :o)

Eve

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