Before I met the love of my life, there was only one other man that I can say I was truly in love with after my marriage ended. But I broke up with him due to a series of events that turned my life upside down and that I thought would cause us to break up eventually... although I can see now that we probably could have weathered these things. Ah, good old hindsight.

Over the years, he popped back into my life exactly three times. And, of course, each time we had sex. I'll bet you can see where this is going, can't you?

Each time we had one of these encounters, I would get all hopeful again that we could work things out and pick up where we left off. And each time, I would get hurt again because he wouldn't call or he would act vague and disappear. I would get all upset and say to myself, "Never again." Yeah, okay.

The last time he contacted me was on a dating site. (Coincidentally, we were both on the same one.) We had some flirty banter, and then one day he sent me an email with the subject: "Your way tonight." He lives a fair distance away, so I knew the only reason he was going to be in my neck of the woods is because he was probably meeting someone from that same dating site. He also persisted with a series of emails telling me how much he was still attracted to me, like a "moth to a flame," he said. He added that he would always be there for me, that I would always hold a special place in his heart, and he always signed off with "xoxo."

I almost waivered, but didn't give in. I succinctly replied honestly that I could never be a FWB with him and that I still had feelings for him which got stirred up each time we met. I never got a reply. (Helloooo, what part about that clear message didn't I understand?)

Long story short, some time after my beloved died, don't ask me why, but I contacted this ex by email. I'll refer to him as "Flyboy" (he flies small planes). Flyboy had also lost someone very dear to him a few years earlier, so I knew he would understand how I felt. And if I'm honest with myself, maybe I was also trying to feel him out to see if perhaps he still had feelings for me. Losing someone to death makes people do crazy things... I was all mixed up emotionally. I was (and still am) very much grieving, but I was also afraid to be alone. I was lonely and scared, and for some reason, Flyboy represented emotional safety and security. Yeah, I know, I know ("How stupid IS this woman, anyway?")

His response to my email offered the usual condolences and advice about allowing myself to grieve. After a few emails back and forth, he told me how he had survived the grieving process by taking a trip to Cuba where he met an "angel" who taught him that life was still worth living, a 20-something Russian girl, and he sent me pictures of him and her together. In case you were wondering, he was probably about 59 at the time. I was a bit shocked by the pictures because I really didn't need to see this gorgeous young girl with him. I mean, really?

Sending me those pictures could only mean one thing, right? He was making a point of showing me that he was WAY over me. Now, this girl didn't become his Russian bride or anything, but it was a clear indication of what he could still attract at his age, I guess. Or maybe he meant for it to be taken as a sign of hope for me that life really can be enjoyed again despite this type of loss.

Yet he also says that he gets down and lonely at times, so that makes me wonder whether or not he has anybody in his life at the moment. Further, a mutual friend of ours whom I haven't seen or heard from in years (but he is still very close to) contacted me on a business networking site the other day. And this guy is not active on that site at all. Is that just a coincidence, or did Flyboy mention me to him? Who knows?

By becoming his FWB, I guess I wrecked any chance of him wanting a relationship with me. I'm thinking his respect for me went down a notch or two because I kept falling for it each time. Why should he want a relationship with someone he can call up and boink any time? Well, that will never happen again, but if I had a fourth chance to meet with him, and we did not have sex, I wonder if our relationship could pick up again. Or maybe it's just too late. Or maybe he's really just a jerk and I should forget about him completely.

Your thoughts, aside from "What kind of a flake are you, sister?" would be much appreciated. Thanks!