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Is he shy? should I bring up dating?

Tagged as: Dating<< Previous question   Next question >>
Question - (18 July 2014) 5 Answers - (Newest, 24 August 2014)
A female United States age 36-40, anonymous writes:

I'm kind of baffled by this guy in my life right now. We've known each other since about the beginning of March. We hang out in a group together, usually to go eat out, see a movie, do some random activity.

We talk the most when we're apart from the group. We also have nice chats through text, and I somehow found the guts to suggest he buy me this food he mentioned some time, though I don't know how that will turn out.

Our text conversation has been really great this week. It just seems like I'm the one stepping forward? He doesn't back off, he just doesn't really initiate. I don't know if he's shy... when we interact it's great. I pulled back a little when one of our friends secretly told me that we should date and I super flustered, but now we're kind of back on track to interacting with each other.

What do you think? Should I just broach the subject with him about us maybe interacting on a new level? He might be leaving soon for school, so that makes this even more uncharted waters for me.... Anyone?

View related questions: shy, text

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A female reader, aunt honesty Ireland +, writes (24 August 2014):

aunt honesty agony auntHi how has things developed?

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A reader, anonymous, writes (22 July 2014):

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

Hi, thanks for your advice guys. We've been chatting more and it's become more comfortable to talk to him in person. Talked to him about some worries at work, he tells me about his long days at work and we chat about things happening in our combined schedules. He's leaving in less than a month, won't be back until who knows when. Maybe for school breaks?

I've braved up and gotten flirty. Told him I thought he was attractive, but I'd only admit it out loud if he bought me tons of ice cream (there's a back story to that...).

Anyway, I feel like I'm at a threshold, where I could do more than just admit out loud that he's attractive (if he does in fact buy me ice cream, haha), or we could just stay in this good friend relationship.

Did I mention he's younger than me? Should have mentioned that. I like him despite that potential barrier, but it still makes me nervous. I know, 4 years is NOT that much, but still. Nervous.

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A female reader, -BMBTL- United Kingdom +, writes (18 July 2014):

-BMBTL- agony auntMaybe just shy and doesn't know what to do, how much do you actually talk about together? Have you flirted with him? How often have you gone out together?

Has he recently broken up with anyone, or has he been hurt in the past etc?

Let me know and I'll try help further! :)

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A female reader, aunt honesty Ireland +, writes (18 July 2014):

aunt honesty agony auntI suggest that you just go for it, you have nothing to lose. If you like this guy then ask him out on a date. It doesn't always need to be the guy that makes the first move any more. Society has changed massively and for the better. A lot of men find it attractive in a woman who knows what she wants and is brave enough to go after it. Look at it this way the worst thing that can happen is he says no. Yes it will be a blow to your ego and you will feel deflated for a while but least you will not be left wondering what if. Plus it is looking good so far so he will probably more than likely say yes. Good luck and keep us posted.

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A male reader, anonymous, writes (18 July 2014):

I think you should,at least you will know where you stand. He sounds a bit like me, I can fancy girls but not have the balls to ask them out. Good luck :)

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