How do I go about asking my (at one time best) friend, whom I just slept with, out on a date?

I met him ten years ago when I was 16 and he was 20. He immediately friend-zoned me because of the age difference and took on a big brother role in my life. We talked every night on the phone. I would tell him about high school, he would tell me about work, and we would both talk about our relationships.
One night I called him crying and he said, "If you were 18, I would totally date you."

Over the years we have drifted apart. Dating other people. Both getting engaged, neither worked out. Moving, changing jobs, changing friends.

We still made time to see each other once every couple years, after devastating break ups or life changes. And one of those times about 5 years ago we kissed. He posted a status on FB that night with the Full Metal Jacked quote "Me love you long time." then added "... just dont turn crazy like the rest."

It was confusing and cryptic. Was that his way of saying he loved me as long as I had loved him? At this point neither of us had confessed any deeper feelings toward each other. I was too scared to pursue it further so once again, we drifted apart.

Saturday was our first time seeing each other in two years. We went out drinking then went back to his place. Neither of us drive because we live in the city so we just take the train, and I had missed my last train of the night so he asked if I wanted to spend the night. It's the first time that's happened and this time when he kissed me, it didn't stop at that. We ended up having sex all night then sleeping together cuddled up in his bed.

I don't want to lose my friend. But finally after 10 year, I am ready to see where things could go with him and want to pursue it.

I want to say something better than "im not assuming that sleeping together means we are going to date, but I just wanted to see if you would like to go on one after all these years?"

I understand that sleeping with me could have meant nothing to him, but I still want to try to see if we could be something.


Most Helpful Guy

  • That was me. It took me several years to realize how stupid I was for not sleeping with those anxious and willing girls. My first was 16 when I was 18. I thought I was a pervert because she was so innocent and naive. I wanted to fool around with her but I never let her know how I felt about her because I did not want her to know I was practically a pedophile. Our society causes these problems to surface. She was more mature both physically and emotionally when I was 18 but who was the one who feared getting caught?


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What Guys Said 2

  • if you were once best friends, just invite him to do whatever it was that you used to do. it doesn't need to be an "official date" or anything like that.

    • I would like it to be an official date though. At this point we are both single, we have both had difficult years and I am at the point where I don't want to keep wondering. We have plans to just hang out again this weekend, but I am ready for it to be more finally after all this time.

    • well, i would be cautious about this. Chances are good if he was your 'best friend' 10 years ago, he wanted to bone you then, and would have been thrilled about some sort of monogamous relationship with you. As such, suddenly coming back to him 10 years later might seem a bit suspicious - he may suspect you view him as a last resort: as though you've had your fun sleeping around but then noticed that you aren't getting any prettier and figured you needed to anchor a guy asap. You should determine if he has become the suspicious type. If so, then your best option is to continue 'hanging out' as you are. As long as you don't pressure him into committing, his suspicions will ease and he will eventually be the one asking you about commitment.

  • I would assume that at this point the both of your are relatively comfortable with each other. I think there is something there that could grow. Don't make it an official date, just go out and hang out at different places. Get to know him, and then make it official if you two so choose it to be.


What Girls Said 1

  • sounds like it was Hot!, I would go for it its worth pursuing. A good friendship is a blessing in a relationship.

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