A
female
age
41-50,
anonymous
writes:This is a bit long and messed up. I broke up with my long term partner ( and fiance) last year. Soon after I broke up, this pretty close friend of mine (call him X) whom I hadn't met for awhile, contacted me to catch up. Not long after that, X broke up with his girlfriend and was devastated (they already had a few problems before). I went out with him a few times to humour him as I had just gone through the same thing and needed someone to talk to as well. It was strictly platonic. X also knew my ex, whom I was still trying to get back with at the time. For several months we hang out together and he even said wanted to fix me up with his best mate (Y). However, over the time, I think he has fallen for me himself (sorry, I don't mean to sound so big-headed, maybe even a rebound). He has asked me casually before if I wanted to go out with him, but I just dismissed it as a joke and I also still couldn't get over my ex. X invited me to a few of his gatherings and introduced me to his good friends, including Y. Y knows that X likes me and even has asked me if I would go out with X. I said I couldn't as I was still not over my ex, besides X hasn't asked me himself. The problem is after that I think I started to like Y, and I think there maybe a chance there. I have a feeling that X will ask me out anytime soon and I don't know what to say. I used to just accept and believe I would like someone over time. But my biological clock is ticking and I don't think X is the type of guy that I am necessarily comfortable spending the rest of my life with (yeah, I probably think too far now, but I think I can say that as I was crashed and burned after the last relationship that I thought would last and I don't want to make the same mistake). Thinking about it, I was probably at fault by leading him on in several occassions too that I thought was just harmless flirting. How do you think I should go about telling X and if there is possibility in getting to know Y better without hurting X? Thanks for reading.
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, puppylove101  +, writes (26 November 2009):
 Whoo! Sounds like you've got alot on your plate. Well, for the first question about telling X, just straight up tell him. Guys hated when you beat around the bush. And for the second question I regret to say either way you're going to hurt X. But, I have a strategy you could use, hook X up or get him to meet someone else. Works for me every time(works better if they both have similarities). Then, later ask Y out. But, if you don't like my answer go with gut.
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