Is it alright to date your best friends younger sister?

About a year ago I hooked up with my best mates sister. It was a drunken fling and something that I was apprehensive about to begin with. I'm 31, and she is 27.

The next day, I told to my friend what happened (excluding details) and he said he is cool with it, but it just means we can never talk about anything. I didn't clarify this, but I assume anything means anything sexual, relationship etc.

He said that she is a big girl and can make her own decisions and he is cool with us seeing each other, I assured him that this was not a one night stand and that I have the utmost respect and admiration for his sister.

Socially, I'm in a position where I see her more than I see him and things have kicked off between us, in that we have been hooking up for the last 6 months regularly. I broached the subject with him one night (minus his sister) and he said it was cool, but once we had a few beers I sensed that he was a little bit funny about the situation... although he didn't admit it.

I figure I should know my best friend of 16 years and know when he isn't comfortable with a situation. I decided to end the relationship and find another girl without the complications.

This didn't go to plan. I couldn't do it. I think she is an absolutely amazing woman and everything about her is what I look for in a partner, maybe because she is from the same vein as my best friend or maybe because we wholeheartedly understand each other.

So, she has now gone overseas for 6 months and is keen to hook up when she gets back. But if I was going to make a break and find someone else, hence avoiding possible complications... this would be it.

Deep down I really like her and I can see myself being with her for the rest of my life, but I really don't want to risk losing the best friend I have ever had through something that is avoidable.

I'm so torn. And the worst thing is I can't talk to my best mate about it.

Does the dating-your-best-mates-sister scenario ever work out?

Should I cut myself loose and try to find love without the complications?

Any advice would be great.

Is it alright to date your best friends younger sister?
2 Opinion