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Do you think he's comfortable enough to meet me alone instead of with mutual friends?

Tagged as: Big Questions, Dating<< Previous question   Next question >>
Question - (9 November 2009) 1 Answers - (Newest, 15 November 2009)
A female Canada age 30-35, anonymous writes:

I hope you dont think im totally stupid for this but ive got a problem wanting to meet up with a friend of mine, we;ve been friends for two years now and i still cant bring myself to ask him to go for a drink one daytime alone. Dont get me wrong this is not a date lol just to go for a drink as mates to cure boredem n have a chat. Thing is if i text him and say me and so n so (mainly my mates that he barely knows if at all) are going into town n does he wanna come he'll come. However before we meet he always asks are the other still going then when i meet him because i meet him before we met the others cuz i have to walk past where he lives to get up there so it makes sense, he will say are the others on there way n stuff.....he seems more bothered about whether the others are coming like he doesnt wanna be left alone with me. Which is why i darent ask him to go for a drink just us two because he will either not come or he'll ask who else is going and want others to go or be awkward like o right..ok and still come.

Yet....he reckons we're good friends,which is what i dont understand because he will met some poeple alone, yea i can see his point in a way because it can get boring just 2 of you but it would be nice to meet up one time.

Thing is i dont no if the past had anything to do with it because from what i could see and what everyone was saying he had feelings for me...big time! but the guys we hung out with didnt even like us being friends....all because of this girl that has known me for ages and had loved this guy for ages and she didnt want me to take him off her so it was hard to be friends yet the way hes acted people always thought there was something there.

TBh though cant see why that would have anything to do with it because we arent around them anymore. The other weird thing is if we talk over the internet im the one that ahs to make the conversation however recently he has started talking abit more rather than giving one word answers which he did back then and the times we;ve met up recently we talk abit more.

Hes not the most confident guy...but yet again hes not shy, hes one of these that around you as a mate and around his mates is all big headed(no joke) confident and is alwyas telling stories about what hes been doing but from what ive seen in the past when something happened(to do with him and this girl thatt btw used him) hes not the most confident guy...he is still it comes to the crunch and then he goes all shy and the reason he became confident with her was because she was always flirting and all over him, but in the end she still had to make the next move.

SO please give me some advice do you think he would meet me alone....its only for a drink as a mate to talk and stuff like you would with anymoree im just not the most confident person and i find it hard to ask him this stuff. I mean i thought thats what friends did? i just dont think he'll meet me, hes like my best friend so i wish we coul just get over what ever this is.

View related questions: best friend, flirt, shy, text, the internet

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A female reader, Legioness United Kingdom +, writes (15 November 2009):

Legioness agony auntRight, this questions been lingering here ages, so wo may not find this of much help but hopefully somewhat useful... You don't get if you don't ask. Ask him out for a drink on a one on one basis, be sure to say in the first place that It'll just be you two, i'm sure you can think up a reason for others not being there? And see what he says, or you're never going to know right? Or even give him a call saying that you're at home and bored and fancy some company, invite him over and say he can bring a friend if he wants. It'd be a start, just having the one other person there opposed to a handful, and if he goes for it, afterwards he should hopefully feel more comfortable being around you on a more intimate basis.

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