How to help make a nervous shy guy feel more confident around you?

[Anonymous]

Hi! My best friend recently started dating this guy. Within time, we ended up going on a lot of double dates with her boyfriend's best friend, whom I find very cute.
The problem is, this guy gets extremely nervous/awkward/shy around me, to the level where he can't even speak to me one-on-one and always needs to be in a group setting! He definitely does not have the guts to ask me out to do something, just the two of us, he never initiates the plans. For example, he'll ask my friend what I'm up to and tell her to invite me to chill with them instead of just texting me..
I really want to get to know him better, but apparently, he thinks I'm very out of his league and it makes him anxious. We have kissed a few times, and I'm always into it, but he's still so hesitant to make any moves. The last time we saw each other, all I got was an awkward hug good night! When we have conversations, he takes an interest in my life, laughs at my jokes, really tries to remember details and gives me compliments, but other than that, he's just extremely fidgety and you can tell it's hard for him. I really try to make him comfortable and ask him questions about himself, etc... According to my friend, he's only like this around me, but I really don't know how to communicate that he should take some more initiative!
If it's relevant, he's 3 years older than me and definitely more experienced (I've never had a boyfriend and have minimal sexual experience. He doesn't know I'm inexperienced though.)

[AthleticMom]

Easy
First the caveat to any successes with such a guy... once they feel they can open up, you might wish to close the lid on this Pandora's Box, as it is likely he's been shut down and worse by normal people exposed to his weird fetishes, be they sci-fi, bondage, social blunders, sexual inadequacies, et al.

Such guys will only expose their socially harmed preferences slowly from hardness snail shells and only under unconditional "everything's OK, no matter what" judgements and encouragements from you, mostly in private (your current venue problem to solve). This includes being the tactile aggressive one, as if touching, squeezing, hugging, even breasts smashing into his chest, biceps is not only natural but expected and invited. Always with the complements, not obvious in public but lathered on in private.
When (not if) he begins to reveal his odd fetishes, you might take the innocent "teach me" posture with enthusiasm to try all new things at least once. He can & will tone down some really odd preferences to suit you with no speaking required on your part, only a gesture or facial... begging that you might get used to it... for him
Aggressive also means YOU invite HIM into more private sessions that begin as innocent outings or at home

[Janieyu]

dont go for this type of dudes ! trust me u'll get bothered even tough they are older than you i mean age is just a freaking number ! trust me i've been there and i know exactly what im talking about.. they tend to hide their feelings a loooot and they have trust issues or else why would he be that shy?

[Nathaniel___]

That’s not entirely true. I have this problem with girls when liking someone and don’t have the balls to ask becuase im so anxious I am.

Reason being is I think I’m not good enough for them and I’m out of there league. Nothing to do with trust issues it’s more of the confidence factor which is the problem.

[SarahsSummer]

Wow, It seems like you've done all the things I was going to suggest. But you may just need to be more forward with him flirtatiously. How old are you? he?

[BrianKang]

It definitely seems like he's into you. I personally can get a bit shy and awkward so my advice would be to keep showing an interest. Once he's had some time to really get to know you he will open up more. Especially if he's not normally so shy. So he's capable of being more outgoing but he's probably just nervous to mess things up.

It may even help to talk to him about it. Let him know you do like him and he doesn't need to feel so nervous around you.

[CheckPlease]

Well with him it seems he likes you and that spooks him. You do also. So with him he needs attention as a friend with a potential to be more.
Simple you and your friends boyfriend needto work with him.
In time and after he gets to know you and that you like him he will relax. Main word being time.
Since he is shy it so take longer than normal.

[Hedgehogg]

Make the moves. Like women, men want to feel attractive and desired.
Clearly he's intimidated and doesn't realize there is no "league" to be in or out of.
He needs confidence in himself. If you're into him, ask him out. Life is too short to wait on someone else to make the moves

[Xasildo]

I say talk to him and try to have an emotionally open conversation. Ask him why he feels so nervous around you and tell him how it makes you feel personally. It helps a lot if you two can get on the same page and become more attuned to each other.

[spartan55]

Is there some rule that says you can't take the lead in social settings. He's just nervous (don't try to figure out why) If you want to get to know him further you will likely have to be the one who initiates things.

[zecky]

That's impressive he's one of the few I've heard that is very shy. He just doesn't want to lose you by making you uncomfortable or he just loves you to the point that makes him crazy like heart rate going more than 120 beats per minute, thinking about what to do next... What you want to do, he's probably the type of guy that in order to start something you have to put the initiative.

[LifeEqualsLove]

Maybe even addressing the fact that you like that he's nervous around you and hope that he'll become more comfortable with time.

Also, some people are just naturally shy and quiet and need more time to adjust to different people's vibes.

[ccscsc]

Brush your hand on his shoulder, touching him just before you sit down or while kissing something like that. Touch is a huge huge signal for guys, thats our most comfortable zone for communicating.

[IronKeks]

I guess he needs more time to get confident with the situation. Some people need more time. Best of luck :)

[Maaa27]

Sorry couldn t read all that but to make a shy person feel comfortable with u is never let awkward silence moment happen

[Steve4783]

Tell him your inexperience let him take charge in the bedroom.
Tell him a bit how vulnerable you are and what you dont like doing because your scared.

[Tholdar]

If he's like me, he won't make a move. Although sounds like he wants to, he just gets in his own way. At this point if you want him you have to make the move.

[DualityGreen]

It will happen over time. Continue to kiss him and everything.

[hiddenmethod]

One of those things a man has to figure out on his own.

[Thomasgun]

His behavior is inexcusable. If he likes you, texting is more or less anxiety than talking in person...

[TallGuy96]

You need to take the lead, for example decide where your next date want to be and initiate hugs, kisses , touches and tell him you like him.

[nemesis915]

Give him some time. I promise he's into you probably more than you think. He seems like a good guy. If you stick with him he'll come out of his she'll.

[wiseguy14]

Talk to her when she's alone ask her why she's shy if she gets more shy tease her

[HereIbe]

So, make a move! You have two functional hands. Once dick is engaged, shyness can disappear.

[Urstupid]

Overtime itll wear off

[unzweideutig]

give him some weed

[weaponsdude]

That'll loosen him up.

[Anonymous]

Suck his dick