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Any advice for dating a shy guy?

Anon, because he might use this and realise it's about him!

So there's a guy in uni who I recenlty got drunk with at a party and he confessed that he's had a crush on me for years... He also asked me out for a drink. I said yes.

He's really cute, and also really sweet, but he's super shy and I'm worried for the date because I don't want it to be awkward. I'm also shy as well, and quite inexperienced with guys (never had a relationship and never had sex) but I realise that for things go well with him, I'll have to make moves and be a bit more forward than I usually am. This is making me nervous because I'm usually too shy to make the first move (eg go in for the kiss etc) so I just wanted to ask for advice.

Are any shy guys on TSR, or people who have dated shy guys, able to help me out? What should I do?

Thanks in advance
Original post by Anonymous
Anon, because he might use this and realise it's about him!

So there's a guy in uni who I recenlty got drunk with at a party and he confessed that he's had a crush on me for years... He also asked me out for a drink. I said yes.

He's really cute, and also really sweet, but he's super shy and I'm worried for the date because I don't want it to be awkward. I'm also shy as well, and quite inexperienced with guys (never had a relationship and never had sex) but I realise that for things go well with him, I'll have to make moves and be a bit more forward than I usually am. This is making me nervous because I'm usually too shy to make the first move (eg go in for the kiss etc) so I just wanted to ask for advice.

Are any shy guys on TSR, or people who have dated shy guys, able to help me out? What should I do?

Thanks in advance


From me being a shy guy (well.. kind of) and having dated, it'll probably get easier as it goes along - you just need to put in that extra effort at the start. So keep in mind some questions to ask to avoid those awkward silences and a drink or two wouldn't hurt his confidence 😂
If you'll pardon the (possibly) out-of-context phrase, some people are showers and some growers. Some are cofident/extrovert from thee outset, others take time to warm to new people/situations etc.

Give him time to get to know you. First couple of dates find mutual interests to talk about, or even just crazy subjects... Something that he'll feel comfortable enough chatting about (or possibly even carried away over!).

As well as the talking, allow for him to also not-talk. Chances are if you don't stare him down during awkward silences (thus making them feel even more awkward) he'll appreciate your efforts all the more.

Depending on if you can afford it (and also if you both drink) suitable amounts of alcohol can always be used to lubricate the tongue and lower any inhibitions - just don't get so inebriated that you dance on tables/shout at inanimate objects/do anything you may regret.

Overall, just go with the flow. If you sense he's not comfortable part way through, suggest a venue change or meeting up again the next day (but none of the "I'll call you and arrange something sometime" which everyone knows is generally a thanks-but-no-thanks in disguise) which will give you both a "second chance".

Source: 26 years' experience of varying degrees of introversion and such.
Original post by Anonymous
Anon, because he might use this and realise it's about him!

So there's a guy in uni who I recenlty got drunk with at a party and he confessed that he's had a crush on me for years... He also asked me out for a drink. I said yes.

He's really cute, and also really sweet, but he's super shy and I'm worried for the date because I don't want it to be awkward. I'm also shy as well, and quite inexperienced with guys (never had a relationship and never had sex) but I realise that for things go well with him, I'll have to make moves and be a bit more forward than I usually am. This is making me nervous because I'm usually too shy to make the first move (eg go in for the kiss etc) so I just wanted to ask for advice.

Are any shy guys on TSR, or people who have dated shy guys, able to help me out? What should I do?

Thanks in advance


He won't be shy once he finds his feet. Dont be pushy, just be patient, which is what you are probably like anyway.
Heaven forbid!
Reply 5
Original post by Anonymous
Anon, because he might use this and realise it's about him!

So there's a guy in uni who I recenlty got drunk with at a party and he confessed that he's had a crush on me for years... He also asked me out for a drink. I said yes.

He's really cute, and also really sweet, but he's super shy and I'm worried for the date because I don't want it to be awkward. I'm also shy as well, and quite inexperienced with guys (never had a relationship and never had sex) but I realise that for things go well with him, I'll have to make moves and be a bit more forward than I usually am. This is making me nervous because I'm usually too shy to make the first move (eg go in for the kiss etc) so I just wanted to ask for advice.

Are any shy guys on TSR, or people who have dated shy guys, able to help me out? What should I do?

Thanks in advance



when you're ready to make the move, get out your smartphone and play him this ..., by the end of it he'll probably end up making the move himself :wink:

Original post by Anonymous
Anon, because he might use this and realise it's about him!

So there's a guy in uni who I recenlty got drunk with at a party and he confessed that he's had a crush on me for years... He also asked me out for a drink. I said yes.

He's really cute, and also really sweet, but he's super shy and I'm worried for the date because I don't want it to be awkward. I'm also shy as well, and quite inexperienced with guys (never had a relationship and never had sex) but I realise that for things go well with him, I'll have to make moves and be a bit more forward than I usually am. This is making me nervous because I'm usually too shy to make the first move (eg go in for the kiss etc) so I just wanted to ask for advice.

Are any shy guys on TSR, or people who have dated shy guys, able to help me out? What should I do?

Thanks in advance

I'm a shy guy, so have never had any luck with this kinda thing.
Keep it goin' with him is my advice.
Original post by SeanFM
From me being a shy guy (well.. kind of) and having dated, it'll probably get easier as it goes along - you just need to put in that extra effort at the start. So keep in mind some questions to ask to avoid those awkward silences and a drink or two wouldn't hurt his confidence 😂


Original post by Mr_Tumnus
If you'll pardon the (possibly) out-of-context phrase, some people are showers and some growers. Some are cofident/extrovert from thee outset, others take time to warm to new people/situations etc.

Give him time to get to know you. First couple of dates find mutual interests to talk about, or even just crazy subjects... Something that he'll feel comfortable enough chatting about (or possibly even carried away over!).

As well as the talking, allow for him to also not-talk. Chances are if you don't stare him down during awkward silences (thus making them feel even more awkward) he'll appreciate your efforts all the more.

Depending on if you can afford it (and also if you both drink) suitable amounts of alcohol can always be used to lubricate the tongue and lower any inhibitions - just don't get so inebriated that you dance on tables/shout at inanimate objects/do anything you may regret.

Overall, just go with the flow. If you sense he's not comfortable part way through, suggest a venue change or meeting up again the next day (but none of the "I'll call you and arrange something sometime" which everyone knows is generally a thanks-but-no-thanks in disguise) which will give you both a "second chance".

Source: 26 years' experience of varying degrees of introversion and such.



Thanks guys! I'm meeting him tonight, we're going for drinks in a bar with pool etc so hopefully I can diffuse any awkward silences with my awful ball skills (no pun intended)

I'll let you know how it goes
Original post by ANM775
when you're ready to make the move, get out your smartphone and play him this ..., by the end of it he'll probably end up making the move himself :wink:



I actually LOVE this song haha, I even thought about sticking it into the OP but then changed my mind

Original post by Nunchuck-master-2334
I'm a shy guy, so have never had any luck with this kinda thing.
Keep it goin' with him is my advice.


What do you mean by never had any luck? Yeah I will do, he seems like a good guy so hopefully with a bit of patience he'll come out of his shell!

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