Dear Miss Emily:

 My situation involves my old high school sweetheart. In Jr. high school I met her and thought she was cute. We became friends and had a lot fun. In high school we dated. I went to the high school prom with her and we had a fun time. We wanted to take our relationship further, become more intimate, and communicate at a deeper level. We believed that sex would have been a way of doing that. We were encourage to wait for sex due to the typical reasons that are given to teens. We did wait thinking that it was the best thing for us. However, we went to different colleges and never did get a chance to express our love for each other in a sexual way. I have had other lovers but none for a while. To this day, I cannot get her out of my mind. I still think of her has as a whole person, being attractive, and wonder what she looks like in the nude. I now wish that we had sex in high school and not waited. I would have liked her as my first. I am certainly curious about what she is like in bed. Our 10 year high school reunion is coming. I hear from a mutual friend that she is coming and not currently in a relationship. Any information about asking if she is interested in continuing our relationship? Any information about letting her know that I am interested in her, wanting to be physical, establishing a bond, and increasing intimacy with her in a sexual way?  Any chance I could have sex with her on the night of the reunion? How could I set it up? Anything I should consider when thinking about her, considering deepening our relationship, or considering sexual relations with her?

--------------------Miss Emily’s advice--------------

If I were you, I'd come back from Fantasy Island and consider other possibilities.  One being that she has not thought of you in the same way and would not be interested, in the least bit, in engaging in a sexual relationship with you.  But if, by some stroke of luck you are on the right track, and she does feel the same way, I would start out by getting to know her, all over again, and take it from there. Do the obvious, ask questions about her last ten years, reminisce about your time with her in high school, how much you think about her and what could have been.  Hopefully, you can judge accurately if she is as interested in you, as you are in her.  However, if your whole goal is to sleep with her the night of the reunion, try not to be too transparent and have a place ready to go to if she is of like mind.  The back seat of your car could work, but know this:  Expectation is more often that not, the road to disappointment.