Is this too harsh?

This guy Harry has been sending me emails and while he’s a nice guy, he keeps bringing up this time that I threatened to handcuff him.

A LITTLE BACKGROUND is necessary here…

A bunch of us were doing a guys vs. girls penny war for a local charity. The guys kept threatening to steal our pennies, so one night at Happy Hour, I turned to Harry, Jon, Frank, and Jason (see, four guys here!) and went, "You boys are NOT going to steal any more of our pennies -- even if I have to handcuff you to make sure that doesn't happen!"

So, fast forward about two years, and Harry's grandfather dies. Kristen and I go to the viewing to show our support. While we're there, his mother starts making conversation, and I realize that this woman seems to know quite a bit about me. For example, even though Kristen's lived in Medfield longer than I (by a year!), Mrs. Pippin seems to only want to know about my experiences and view on the hood. She also knew what I did for a living, and all sorts of other bits of random trivia about me.

A week after the viewing Harry offers to take Kristen and me out for dinner to show his appreciation. We let him (free food after all!) and he starts bringing up handcuffs. Initially, I don't remember, but as he's going on and on, I do start to form some recollection. He also "tosses" himself at me during dinner...even though Kristen is right there. However, I don't react to any of it.

Then, a bunch of us are out again two weeks ago, and he brings up the damn handcuffs again. I even ask Jason to the wedding right in front of him and though I'm forced to mention that Jeremey and I are no longer an item, I make it clear that I'm moving on quickly. But no, even when I'm not paying attention to him, he's telling the other people at the table about the handcuffing incident!

Since then, he's sent me a few emails "just checking in," no mention of cuffs, but I haven't responded. I feel however, that I owe him an explanation and a bit of a lesson in why, though he's very nice, I'm not interested in pursuing a real friendship with him. Up to now, we've really been acquaintances, and he asked me out a few years ago, but I put a stop on that real quick.

My dilemma is that a) I'm not experienced at being particularly mean b) his grandfather's only been dead for about a month and c) he's had some medical problems that have made him a little awkward (he had a stroke when he was a little kid). Therefore, being too mean would be like kicking Tiny Tim and then taking away his crutch.

So, I'm thinking of sending him this. What do you think?

Harry~

Yes, all is well and my review went brilliantly. Thanks for wondering.

I guess you've probably been wondering why I haven't emailed you back until now. The truth is that this constant bringing up of the handcuffs has been making me very uncomfortable. I go to your grandfather's wake to show support to you and your family, and you choose to show your appreciation with public accusations of threatening to perform sexual acts that I a) never said I was going to perform and b) never specifically said I was going to perform on you. If I remember the incident correctly (as you have now forced me to do), any threat of handcuffs was a light-hearted joke in reference to keeping you and the three other individuals who received the same threat away from our pennies. The others haven't been bringing it up all this time, so I can only assume that they took it in the spirit that it was intended and that you somehow haven't.

I know that you think you're joking, but it's really getting to not be funny. Harry, you're a nice guy, and I consider you a friend. I like to joke around with my friends, but I can't joke around with you if I can't be sure that you're not going to take what's clearly a joke and use it to imply things about my sex life. It was so long ago that those who were there (including me up until recently) have forgotten most of the details, and you're conveniently leaving quite a few parts out when you share the story. The result is that you're implying quite a few things about me that I'm not too happy to have out there. It's also made me wonder what other light-hearted, off-hand comments I may have made to you in the past that are now circulating the halls of T. Rowe Price or the Jaycees.

I don't want to make things more uncomfortable, so let's just drop the whole thing. You stop bringing up handcuffs, and I'll know that you've stopped, and we can totally move on without having to discuss this again. I don't need an apology or anything, because I'm not mad. I just thought I should say something before it gets too far out of hand.