There's no shortage of these, but the chart below focuses on women with whom I had an extended friendship/dating-type relationship. I have always had problems with closing the deal--by that I mean switching over from casual dating or friendship to something more serious, something clearly defined as a relationship, where there's a boyfriend and a girlfriend and all that that entails.
In my life, I've gotten around to the "talk" five times, and each time the result has been, "Let's stay friends, as I'm not interested in something romantic." Here's how long it took for me to get to that point with each gal:
So why does this always happen? (And I'm not being hyperbolic since I've never had a "yes" and thus never had an official girlfriend.) I think there's a combination of factors. One, I probably send off friend signals too much rather than romantic signals (especially because I really try to avoid too much physical touching: I'm more a believer in "courtship" than "dating"; that is, I don't want to do anything with a gal I wouldn't do with anyone else until a relationship is formalized--and wouldn't do most things until the wedding). Still, there are verbal signals one can send, and I really tried to do that before I got rejected this last time a few months ago, but alas whether it worked or not--I still got the same result. Another may be that my asking has often been part of a sense of panic rather than calm: another guy seems to be moving into the picture, one of us is moving away, the gal is spending less and less time with me. Hence, it's been bad timing on my part.
In some cases, part of the reason I asked, though, was so that I would know where I stood with regard to dating so that I could pursue other opportunities without guilt. So in that sense, I was trying to be honorable to the woman I'd been seeing. Sometimes, the "no" was a partial relief, sometimes not--depending on how real and immediate those other opportunities were and how interested I was in pursuing them.
I suppose one good thing for those who I ask is this: they end up
married within a few years. The only one still single is the one who
just rejected me. How long will she stay on the market? We'll see.
This other chart shows the time it took to end the possibility of a relationship with women I went out with for a period, who I never got around to asking for one reason or another: (1) I had serious intentions but the gal made clear we would only be friends before I ever got to a point where I felt certain enough about my own goals to ask; (2) the gal rejected me by disappearing because I wasn't sufficiently into her (which is true: I probably never would have asked); or (3) the gal threw herself at me (i.e., she brought up "the talk" rather than me), and I had to turn her down (in each case we remained platonic friends afterward, as we were before).
It's easy to boohoo when I get rejected, but the above chart shows that I've disappointed my share of women as well (and I'm probably not even listing all of them, since there wasn't a formal time when I had to do the rejecting in most cases).
I used to think it was easier to get rejected than to reject, but when I think on those friendships I've charted above, the hardest ones, in my memory, have been those I was rejected by. What I think I really meant, when thinking that rejecting was harder than being rejected, is on the short term: after one date or something like that, because it feels much more superficial in those cases: how can I reject this person to whom I have hardly given a chance and who by every indication is wonderful but who doesn't at all light my fire and who I suspect never will? Cases, in other words, where my heart says one thing but my head another. If the yellows in the bottom chart had actually asked rather than disappearing, perhaps my feeling would be that rejecting is harder, since two of those were clearly head versus heart cases.