A
female
age
36-40,
*untonnie1986
writes:Hi AllBasically, I want some help to know whether i should start dating my friend.Im 26, single and live in Perth Australia. His name is "Daniel" and we have been friends and worked together for three years (we both have our own businesses and write each other into projects). We travel across Australia together for work alot and he and I would often go to clubs together though I usually go home with other guys.We have slept together once, in a drunken state, a year ago, but I brushed it off as an innocent, albeit fun mistake. He is cute and very sweet and I know he has a major crush on me. I have probably taken advantage of that a little (e.g. he has picked me up from other guys houses before and driven me home when I cant get a cab in the morning).Anyway, after three years of dancing around it, he finally asked me if I was interested in a relationship with him. I was a little shocked becuase he didnt ask to go out, just went straight to boyfriend/girlfriend. I said I had to think about it, and so am.I really like him and know he would do anything for me. He makes me laugh and I enjoy spending time with him. But I am pretty free sexually and enjoy being with more masculine and dominant men. He is the shy reserved type that Im not really sexually attracted to though emotionally love. He told me that if I agree, I can continue to "be free" which means sleep with other men. While I find the idea attractive (i.e. being in a relationship and still having fun with other guys), I dont know whether I would be comfortable cheating on him even with his permission. I have had a tendency to really use and destroy nice guys before and while Dan probably knows better than most what he is getting himself into, I am really torn taking him up on his offer.The problem is I probably will say no to him if I dont think I can live how he has suggested. The "freedom" is definitely an attractive part of the proposition and as much as I like him, I know I would cheat on him with or without his permission. But saying no will potentially risk our friendship and Im worried what the rejection will do to Dan and his confidence. I dont want to lose our friendship but I think there is a chance I am going to lose it either way.So, should I date my friend, likely cheat on him with his permission, and risk our friendship or say no, hurt him and risk our friendship. Being selfish, I say hell yes date him, especially since it is his idea for me to continue to sleep with other guys. But Im trying not to be selfish in this decision and want the best for him too.Any help would be appreciated.Ronnie
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female
reader, fishdish  +, writes (23 June 2012):
 This seems like a mutually agreed upon concept, that you are out of his league, which is sort of a disturbing premise to start something, don't you think? Originally I suggested dating so that you would become more invested so as to not hurt him. I know he says he's ok with it, and even likes the idea of it, but not knowing him, I think he comes off insecure and like he doesn't DESERVE all of you, so I'm less sure about where it's going. Even though you both know the terms of the relationship I'm not sure what you get out of it and I feel like it's ultimately going to hurt him. Just ensure with yourself that he's strong enough to handle what he says he can, that he's not a pushover or just doing this because he wants at least PART of you when you both agree he doesn't deserve the whole package. Sorry if this comes off harsh.
A
female
reader, Funtonnie1986 +, writes (11 June 2012):
Funtonnie1986 is verified as being by the original poster of the questionOk so now we are unofficially dating and so we chatted about me with other guys. I thought he was sacrificing something by letting me do it but it seems he genuinely wants me to. Says he likes the idea. Also said he knows I'm way out of his league and it's only fair to share me round. Now I think I want to take him up on the proposition.
Thoughts?
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A
female
reader, Funtonnie1986 +, writes (10 June 2012):
Funtonnie1986 is verified as being by the original poster of the questionOk. So I went out with him last night and I didnt stray and instead spent my time with him. Dan is a great guy, if a little friend material. I do wish he was more my type but he is sweet and kind and dotes on me. I know he would never hurt me.We didnt sleep together but we did fool around a bit. I am a lot more experienced than he is so its like im training him which is fun.We travel back home to WA tonight so I will start the formal test run next week. Not official as you so we can see how it goes.
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A
female
reader, fishdish +, writes (9 June 2012):
exactly! win win- best of luck :)
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A
female
reader, Funtonnie1986 +, writes (9 June 2012):
Funtonnie1986 is verified as being by the original poster of the questionThat's a great idea! A bit of a test run so to speak. Thanks for the response.
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A
female
reader, fishdish +, writes (9 June 2012):
why don't you suggest the middle ground that you want, that you two start dating but are not 'official' yet and have time to determine if you can see yourself being monogamous with him? While you think you know him right now, maybe in a dating setting you'll get to know a different side to him, and you might be more willing to settle down with him when you see that. I think this way you can test things out a little without committing to a lifestyle you don't think you can swing.
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