What might have been

by Dating Goddess on November 19, 2010

Sometimes we find ourselves thinking about someone we would have liked to date, but it never came to be. You wonder how it might have turned out. If he’s still single, you wonder if you should reconnect. Or if he’s now a pal, if we should telegraph our romantic interest.

A colleague and I found ourselves single during the same time frame. We enjoyed each other’s conversations, but there was never any move to go out. We shared dating stories and cheered each other on. He was always attentive and complimentary, but he never intimated that he felt other than pals.

A year ago he started dating a woman and became engaged. I was glad he’d found someone who adored him as much as he did her.

I saw him recently and updated him on my dating status. He asked how many men I’ve now gone out with. When I told him 105, he said he wishes he’d been in the mix.

I was surprised since I knew he was in love with his fiancée. I had no idea he would have liked to go out with me. We live several states apart, so it would have been hard to date seriously. But his comment did make me think of others I would have liked to have dated, to see if it would have worked out.

Do you daydream about men who got away? That you would have liked to have dated but it didn’t happen for whatever reason? If so, have you made contact to see what might evolve? Tell us your story.
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{ 4 comments… read them below or add one }

Mitsy November 19, 2010 at 10:04 am

Actually, it’s interesting if you think of the men “friends” you’ve had over the years and how it never evolved into anything more than friendship. For the most part, I think it’s OK for it to remain as friends forever as some relationships are not supposed to turn into anything more.

For me, I had a guy who was in college when I was and we hung out a lot as friends but never really dated. He was more of a big brother figure for me than anything else. Once we were both out of college & working, he took me out a couple times as a date. He started talking about his friends getting married & what he wanted in his wedding. It was like he decided he was going to get married & started the dating process w/me. He talked about sending me flowers and I soon realized that I needed to end this dating situation as I simply had no physical attraction for the guy.

I did care about him but the one time we kissed, it was like kissing your cousin. Zero sparks. It was awkward and painful to tell him that I was interested in another guy but that was the truth. My life would have been easier (in some ways) if I had stuck with this guy, however, I didn’t love him in that way and knew that the physical attraction would not grow. Our families had gotten along well and I think my Mom still wishes I’d married this guy. I have no regrets about it though. He went on a cruise and married a gal he met there. They have been married about 25 years now and have 2 kids. I occasionally run into him when he comes back to town, but I know that I would not have been happy married to him.

I have other stories, but he was probably the only one who was truly interested in getting married.

Mark November 19, 2010 at 12:01 pm

It’s never happened to me. I was in a long, long marriage and since my marriage I’ve dated every woman who interested me and had several serious relationships (I’m in one now).

Before my marriage I essentially went from one girlfriend to the next. I never had too many; I had long-lasting relationships for the most part, or else it was one date and done.

The only thing I wonder about is the first girl I fell for. That didn’t work out due to something beyond our control. That’s the one I wish had worked. She was my best friend for so many years.

Beth November 21, 2010 at 2:07 am

There was a boy in my high school choir class that I considered a friend, and I thought that was how he felt about me as well. Until the last weekend of our senior year when the choir took a trip to another town. My friend looked older than he was, and the drinking age was 19 back then, so he hit the liquor store and he and his roommates had a party in their motel room. We drank and watched Saturday Night Live and laughed and he said some things that led me to believe that maybe he liked me as more than a friend. I hoped.

On Monday, he caught up with me and told me that he hadn’t met anything he’d said. Hope died. Two days after that, we graduated. He went on to Basic Training. A year later I got married. We saw each other on and off at things like the choir teacher’s retirement program, an alumni choir thing, school reunions. Sometime between the 10th and 20th reunion, he got married. At our 30th reunion, I was divorced, but he was still married.

Our 35th reunion approaching, I met up with another classmate who told me that our mutual friend was now divorced. I found myself wondering what might happen… if there was still any attraction…. Then, I got a message from that same mutual classmate telling me that our friend had passed away.

At the memorial service/celebration of life, there were four of us from school. We sat together and laughed and reminisced. One of the guys exclaimed to the other guy, “Hey! Remember how crazy in love he was with Beth?” I was flabbergasted and listened as they told me how my friend would drive my house each night, how it broke his heart when he heard I’d married. And I sat through the rest of the service wondering what might have been if, instead of apologizing, he’d have asked me out. I still wonder and think that sometimes… those what ifs… they can break your heart.

Yvette Francino November 21, 2010 at 8:11 am

Interesting question… I’ve had quite a few very good male friends and when you’re both single, the question probably comes up in both of our minds… should we bump the status up to a dating relationship?

Usually, I don’t want to date men who have been my friends because I’m afraid of losing the friendship. It’s very difficult to move backwards in intimacy, so if I don’t feel confident that it will work out, I don’t want to risk it. I’d have to be really very attracted to someone to move out of the friend zone, and usually, I have fond feelings for my friends, but not super-romantic feelings…

If I ever do get those urges to move to a dating relationship, I will act on it… either by being very flirtatious or just outright suggesting a date… Then the ball’s in his court…

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