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How do proceed with dating this shy older guy?

Tagged as: Age differences, Dating<< Previous question   Next question >>
Question - (4 February 2014) 3 Answers - (Newest, 5 February 2014)
A age 36-40, * writes:

Me and this guy have been in touch for nearly 2 months, from the first day we met. After spending loads of time talking to eachother online, we finally had our very first date the other night. He was very shy, considering him being 34 and me 25, I was quite surprised how shy he really was.

We had a coffee first, spoke for a good few hours about lots of things, he seemed really interested, kept eye contact with me all the time, always tried to make conversation, but he seemed a bit tense, like he was a nervous. After our coffee, I suggested food, and he accepted, so we went for a meal which was really nice, and treated me to food too, which I didn't expect, and we then headed off home.

When he got home he messaged me saying "Thank you for the lovely evening! It was great to finally have a good old chat and hang out. Hope you had a good time too?" But no mentioning of meeting again. But hes been speaking to me none stop since the date, so I assume there's interest?

He is generally a lovely guy and I hope he feels the same. I didn't feel anything negative during the date, but I'm worried about a follow up. I really want to see him again, but I shouldn't have to encourage him to ask me out again. (Before our first date he said, next time your free we can go for a coffee) so I had to encourage our first date to happen saying "so when you taking me for that cuppa you promised :)". And he then followed it up. But even after the first date, he still hasn't asked me for my number. He just uses facebook as the only source to talk to me.

What should I do? Do I have to be a bit more patient with him, as hes too shy? Make more first moves? Or is he not really into me?

View related questions: facebook, shy

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A reader, anonymous, writes (5 February 2014):

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

Thanks very much for your responses guys! Yea I guess I might have to take some initiative, but I'll give it a little more time. Last thing I want is to scare him off.

And yes I did reply, I thanked him for a wonderful time, and that it was nice seeing him. I just need to help him come out of his shell. I dont like the idea of me being in control all the time. I'd like him to do some asking on his own too.

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A female reader, So_Very_Confused United States +, writes (5 February 2014):

So_Very_Confused agony auntdid you respond to his message? did you tell him you had a great time and can't wait to do it again?

that would be my first step. He may be afraid to ask... and having an idea that he won't get shot down may help.

also you can send him a FB message with your cell number saying "it will be easier to communicate on the phones directly don't you think, here's my number" and then see what happens.

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A male reader, anonymous, writes (5 February 2014):

He sounds interested allright.

Judging from what you've told us, I'd say that, aside from being shy and introverted, he might well have a social phobia or anxiety problems. He reacted in pretty much the same ways I'd react, and I've got a bad case of social anxiety.

If that is the case, then you're going to have to take the initiative if you want things to go anywhere with this guy. Waiting for him to ask you out again is propably not going to work. If he really is attracted to you - and I'm pretty sure that he is - his shyness and anxiety will only make him even more reluctant to act. He'll be outright terrified of the possebility of making any mistakes with you.

There's also a good possebility that he's genuinely wondering about wether *you* are really that attracted to *him*. "Is she really interested?", "Will she respond well if I ask her anything?", "I'm not just bothering her, am I?" - if he's anything like me, then odds are that his mind is buzzing with such questions right now.

If you want to counteract all that, then, like I said, you're going to have to take the initiative. Make clear to him that you like him as more than just a friend, and don't be affraid of asking *him* out.

His shyness and reluctance won't immediately disappear, but it should at least be enough to help him get out of his shell.

Also; considering what you said about his extreme shyness and all, there's a good possebility that he has little experience with dating and relationships (in fact, he may not have any experience with this at all). It could explain why he is doing (or not doing) certain things, like asking for your number right at the first date.

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