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Should I try to initiate a relationship with him even though he isn't a fan of such?

Tagged as: Dating<< Previous question   Next question >>
Question - (17 February 2013) 3 Answers - (Newest, 17 February 2013)
A female Canada age 30-35, anonymous writes:

I have always had a thing for my best friend and he recently told me that he likes me. He isn't a player but he doesn't like having a girlfriend because in the past they have always gotten clingy and caused drama. I feel a really connection between us though when ever we are together and we've been spending a lot of time together lately. I'm not sure what I should do. Do I try to initiate a relationship even though he isn't a fan of them or would it be best to test it out and see if he will change his mind if we start doing things. I am a bit timid to discuss his opinion on us dating since I value out friendship and don't want it to be ruined but at the same time I think we could be great together.

View related questions: best friend, player

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A female reader, CindyCares Italy +, writes (17 February 2013):

CindyCares agony auntI tend to agree with Ihavetoomanythoughts. If someone tells you they are not into relationships, listen to them. They mean it, and there's a reason why they bring it up, it's a conscious or subconcious disclaimer. It's a " don't even go there " just in case.

I think nobody is pro or against relationships per se. Almost nobody wants a relationship, ANY relationship, just for the sake of being in one. And almost nobody would refuse on principle a relationship with someone special who'd really capture their senses and mind.

The mental proviso ,so, is " I don't do relationship, unless I chance into someone really exceptional who takes my breath away ".

And that would not be you. Not because there's anything intrinsacally wrong with you of course. Anyhow, he just told you, indirectly, that he's not got the interest, time and patience in doing the " slowly getting to know you and see what develops " kind of thing with you. He needs something more, something different, to make him put in the effort. It means there's nobody yet ( including you ) striking enough, alluring enough , to make him sacrifice his comfort, freedom and habits . The moment he'd meet her, his fear of " clinginess " would disappear. It's mathematic :). Who knows, maybe he'd become the clingy one.

All in all, I'd pass this one, I'd look for someone already more receptive to your charm. I don't know, maybe it's because personally I am kind of lazy, but I don't really believe in struggling to win someone over. Isn't it better to follow the path of least resistence ?

I mean, suppose that you are a fitness buff who wants to convince a couch potato friend to train with you for a long distance race. You'd have to beg, to cajole, to insist, to sulk, to convince them about the benefits of running, you'd have to invest a lot of time and energy, and take a lot of rejection before you make them do what you want.

At this point, isn't it simpler and happier to just choose another fitness oriented, sport enthusiast friend to train with you ?

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A male reader, CMMP United States +, writes (17 February 2013):

I was like that at his age. I'll tell you what, when I finally let my guard down I was happy.

Take it slow with him and you shouldn't have any problems.

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A female reader, ihavetoomanythoughts Australia +, writes (17 February 2013):

ihavetoomanythoughts agony aunt"would it be best to test it out and see if he will change his mind if we start doing things" I think this isn't a good idea. That sounds like a friends with benefits relationship to me, which actually seems like what he wants. Good for him but bad for you because it appears like you've got a greater emotional investment in this than he does.

He doesn't want a girlfriend because she MIGHT be clingy and cause dramas?

Or could it just be that he's not willing to put the effort in?

If you like him, then it should be a relationship or nothing more than just friends. If he likes you, and you're best friends, then he should have a pretty good idea if you could be the ideal girlfriend. Just ask him out.

If he's not willing to get into a relationship but starts to make advances on you, then you know what he really wants. And if you guys do become more than friends, still take it slow. It doesn't matter how long you've known each other, you still don't know the intimate sides of each other to start having sex immediately! Make it long and sweet like if you were dating a new person.

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