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How do you go about expressing interest to a shy, inexperienced guy?

He's 19 and never had a girlfriend and generally speaking is not very experienced with women. He is quite sociable and does lots of extra curricular activities but he is shy with women. I really fancy him but I don't want to scare him off by expressing interest. I try to drop hints but again I think he is just so shy with women that it makes him oblivious. I'm getting kind of frustrated now should I just tell him that I like him as more than a friend? I feel like even if he likes me back he might never make the first move.

Thanks :smile:

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How long have you known him and how much do you two speak?
Be clear and unambiguous: "I'd like to go on a date with you". If you don't think he has any idea about where to go, suggest somewhere.

He may say no, but if you don't ask, he probably never will.
Reply 3
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Oh ooo
1
Original post by Anonymous
He's 19 and never had a girlfriend and generally speaking is not very experienced with women. He is quite sociable and does lots of extra curricular activities but he is shy with women. I really fancy him but I don't want to scare him off by expressing interest. I try to drop hints but again I think he is just so shy with women that it makes him oblivious. I'm getting kind of frustrated now should I just tell him that I like him as more than a friend? I feel like even if he likes me back he might never make the first move.

Thanks :smile:


Well you just said that he was "quite shy around females", and oblivious to the signs, so you pretty much answered your own question. You have to be the one to approach him, has he obviously won't, so you need to make the first move.

If you don't he won't and both will be stuck in limbo, wondering what could have happened.:wink:
Reply 4
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Original post by TheSexyApple
How long have you known him and how much do you two speak?


We've known each other a few months and see each other 1-2 times a week, but mostly as part of a group. We speak each time and he usually comes over to talk.
Original post by Anonymous
We've known each other a few months and see each other 1-2 times a week, but mostly as part of a group. We speak each time and he usually comes over to talk.


Get alone with him somehow. Either on the bus or having lunch. And start a convo. Then be like so do you like anyone / are you interested in anyone. See what he says. If he says no it's perfect for you to be like "I think you're cutee"- do you maybe wanna take our rs further. and he'll obvs say yeah
Reply 6
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Original post by unprinted
Be clear and unambiguous: "I'd like to go on a date with you". If you don't think he has any idea about where to go, suggest somewhere.

He may say no, but if you don't ask, he probably never will.


I know I think I am going to have to be the one to ask him at any rate. I just pray he doesn't freak out :mmm:
Original post by Anonymous
I know I think I am going to have to be the one to ask him at any rate. I just pray he doesn't freak out :mmm:


Maybe ask him for his Skype or Whatsapp or something, talk to him and steer conversations so that you can see how he feels about you.
Reply 8
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Original post by Oh ooo
Well you just said that he was "quite shy around females", and oblivious to the signs, so you pretty much answered your own question. You have to be the one to approach him, has he obviously won't, so you need to make the first move.

If you don't he won't and both will be stuck in limbo, wondering what could have happened.:wink:


Yes I hate being in limbo! Best to even be rejected than be in limbo.
Reply 9
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Original post by SeanFM
Maybe ask him for his Skype or Whatsapp or something, talk to him and steer conversations so that you can see how he feels about you.


I have his whatsapp... I don't think he uses it much. Can you think of a good random convo starter for me?
Original post by unprinted
Be clear and unambiguous: "I'd like to go on a date with you". If you don't think he has any idea about where to go, suggest somewhere.

He may say no, but if you don't ask, he probably never will.


By the way what kind of date should I ask him on? Lunch? Coffee? Cinema? Dinner? Drinks? Other?
Original post by Anonymous
He's 19 and never had a girlfriend and generally speaking is not very experienced with women. He is quite sociable and does lots of extra curricular activities but he is shy with women. I really fancy him but I don't want to scare him off by expressing interest. I try to drop hints but again I think he is just so shy with women that it makes him oblivious. I'm getting kind of frustrated now should I just tell him that I like him as more than a friend? I feel like even if he likes me back he might never make the first move.

Thanks :smile:



Stop faffing around and ask him out. Never mind this he's really shy around women, just do it
Although you haven't explicitly said it, the implication is that you aren't as shy and inexperienced with the opposite sex as he is. So it seems that you've got nothing to lose if you're the one pushing this forward. Obviously I can't say if he really does like you, but he might do, and in his mind, he probably feels like there is a lot for him to lose if he's the pushy one.

So, take the lead on this, and try to subtly indicate to him that his inexperience doesn't put you off.
Original post by Anonymous
I have his whatsapp... I don't think he uses it much. Can you think of a good random convo starter for me?


'You got a bae or nah?'

Or 'there's this movie about (insert something kind of related to his interest or films that he likes), d'ya wanna go and see it?'

...I can't think of any random good openers either.
Original post by silverbolt
Stop faffing around and ask him out. Never mind this he's really shy around women, just do it



Tough love :smile: But yes you are correct!
Original post by Anonymous
Although you haven't explicitly said it, the implication is that you aren't as shy and inexperienced with the opposite sex as he is. So it seems that you've got nothing to lose if you're the one pushing this forward. Obviously I can't say if he really does like you, but he might do, and in his mind, he probably feels like there is a lot for him to lose if he's the pushy one.

So, take the lead on this, and try to subtly indicate to him that his inexperience doesn't put you off.


Yeah I'm a few years older than him and I started dating at his age. Yes I will have to show him that I don't mind him being inexperienced I find his shyness very cute but also frustrating!
Original post by SeanFM
'You got a bae or nah?'

Or 'there's this movie about (insert something kind of related to his interest or films that he likes), d'ya wanna go and see it?'

...I can't think of any random good openers either.


The bae one made me laugh :biggrin:
U sure he isnt gay tho?
Original post by Anonymous
Yeah I'm a few years older than him and I started dating at his age. Yes I will have to show him that I don't mind him being inexperienced I find his shyness very cute but also frustrating!

Fair enough re. your frustration, but speaking from the other side of the fence, it's debilitating not knowing whether it's gonna be an issue or not. You only need to look at the countless threads that come up on this very website to get some insight into what might be going on in his mind. Going by what's on TSR, it seems like unless a male is perfectly configured (in terms height, weight, sexual experience, and, well, everything, really), most women will just callously disregard him, or ultimately snub him. Hardly any wonder he's petrified about putting himself forward if he feels humiliation is the likely result.
Original post by Anonymous
Fair enough re. your frustration, but speaking from the other side of the fence, it's debilitating not knowing whether it's gonna be an issue or not. You only need to look at the countless threads that come up on this very website to get some insight into what might be going on in his mind. Going by what's on TSR, it seems like unless a male is perfectly configured (in terms height, weight, sexual experience, and, well, everything, really), most women will just callously disregard him, or ultimately snub him. Hardly any wonder he's petrified about putting himself forward if he feels humiliation is the likely result.


Hmm that's interesting... I was always dismissive and thought that the guys who were hung up about those kind of stuff were just chasing the wrong girls i.e. the shallow hot girl types but that is just my view (most women? really?) but maybe I'm wrong. Those things don't really matter when it comes to making a lasting relationship, which is what I'm after. But yes you are right he is probably terrified and maybe he has those thought too and is scared of measuring up, in which case the least I could do is make the first move.

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