How do you know when it's the right time to start dating a close male friend?

I'm afraid of starting a relationship with my friend.


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Most Helpful Guy

  • You dont. The only way to tell is to try - I have been struggling with this (but with a female friend) for a couple of years now. I have seen people try and fail, and I have seen people try and succeed. More details would help, but in general - how close of friends are you? What do you do together, what does he do/act around you? You can try asking mutual friends, but there is always a chance that it will get back to him before you want it to. Right now though, I would say go for it - if he is truly a close friend he will not fault you for liking him, and you will still be friends (if he does not reciprocate the feelings). If he stops being your friend for it, was he really the kind of friend you wanted? Or he will return your affections and you will now have a close boyfriend. Good luck!

    P.S. If you give more information I can help more, this is just assuming a normal guy with normal feelings and qualities.

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What Guys Said 1

  • I'm also in a similar situation. Dating a friend can be quite worry some, risking your friendship if it goes wrong, but if it turns out well, it could prove to be a great relationship, as you've already gotten to know each other quite well and are obviously similar as you're still friends.

    He could be thinking the same way you are... If you feel it can work out, than I defiantly recommend making a move! :)

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What Girls Said 1

  • That's very risky..I wouldn't advise it. I'm dating my best friend and he and I have been having problems for a year. If you feel strongly about wanting to date him, I suppose give it a shot but he may not be there in the end =/

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