The 'Should Have Been' Dating Order

(This is an exclusive, as it’s more personal than something I would put on Facebook).

Out of the blue, I had this thought one day: what if I dated the same women that I have dated, but in a different order or at a different time? Would things have gone better? Hmm. We’ll let’s see what happens when I “think aloud” about this.

*Before I get started, I in no way want to get back with any of my ex-girlfriends. While none of them are bad people, I think there’s a reason I’m not with them anymore.

Even though this isn’t on FB, I’ll still avoid using real names and all that. Just makes sense.

Note: when I say “should have dated”, it corresponds most with the age I was when I actually dated whoever was actually in that position. For instance, if I say I should have dated someone fifth, it means they were best for me when I was 24-26. I’m pretty sure y’all would have figured that out, but just in case….that said, it will still go in order.

Angela

Actually Dated: 1st (My Age: 19)

It was really clear that I was looking for a relationship, as I was the nose-wide-open young guy that we all are when we enter our first dating experience. (Yes, ladies: this time actually exists with us). Had I had my eyes open instead of my nose, I’d have seen that she wasn’t. When you have two people who want completely different things, you can easily predict how it’s going to turn out…and that’s how it turned out.

Should Have Dated: 4th

She’d have been the perfect follow to the woman I should have dated third, and also the one who would have sent me off into the stretch of singlehood that I had after dating the actual fourth woman. I could have easily seen myself saying “I’m doing me” after dating her if I had enough experience and awareness to know to do that.

Ann

Actually Dated: 2nd (My Age: 20)

Learning the lessons from the previous experience, she and I talked a lot about what we wanted and it seemed we wanted the same things. Everything was going along great until I told my parents about her (because she had children). They hated her from that point on - but had never met her, and she started to push herself away because of that. It took me two and a half years to forgive them over that. She and I kept in touch sporadically after we broke up, and I went to visit her a few years ago. She’s married now.

Should Have Dated: 6th

This is pretty easy: I’d have been old enough (according to my parents) to date someone with children, which would have taken away their complaint. Who knows: she might have been married to me…but I’m actually glad she isn’t. Her looks went south between the last time I saw her and her wedding day.

Elizabeth

Actually Dated: 3rd (My Age: 20)

Here’s the funny thing: I knew Elizabeth for a year before I even met Ann. She and I had gotten really cool over time, but never thought about dating each other. Of course, I was all too happy when Ann came along and she was all I ever talked about. Elizabeth was genuinely happy for me and was a great friend. When Ann and I broke up, she was right there and actually admitted that she was a little bit happy. I asked why and one thing led to another before we got into a relationship ourselves. Well, the breakdown of my relationship with Elizabeth was completely my fault (even though friends of mine who know everything feel otherwise). That’s the one relationship I’ll say that about.

Should Have Dated: 1st

I think ideally when you go through your first dating experience, you want it to be with someone that you’ve built a solid friendship with. I imagine it would make things a lot easier as you try to figure things out as a couple. Even if things go awry, you’re not as likely to be jaded as you’ll hopefully still have the person there as a friend.

Vontrice

Actually Dated: 4th (My Age: 21)

In case anyone’s wondering, I’m using their middle names (no, I could not think up ‘Vontrice’ on my own). She was the first girl I dated who didn’t try to match my relationship intensity. This wasn’t a problem at first because, well, I wasn’t that intense about it. As things progressed, I locked into full relationship mode and she didn’t. One thing I can’t stand when it comes to relationships is the feeling that the other person doesn’t respect the relationship as much as I do (this will come up again). Eventually, she said - well, nodded - ‘no mas’ and that was it.

Should Have Dated: 3rd

I think this would have been a good time for me to be broken in to the idea that not everyone approaches relationships the same way. Funny thing is I met her a month and a half after Elizabeth and I broke up, so there’s not a lot of difference in terms of me between the times I dated the two anyway.

Nicole

Actually Dated: 5th (My Age: 24-26)

There was a lot of good with Nicole. There was a lot of bad with Nicole. The good with Nicole was probably the best of anything in any relationship I’ve had. The bad with Nicole was definitely the worst of anything in any relationship I’ve had. I’m not going to go through specific moments, but suffice to say our relationship was very ‘polar’. She would probably be one of my best friends (definitely would be, out of the women I dated) if not for the relationship. Oh well.

Should Have Dated: 5th

If I dated her before I got a little bit of experience, I’d probably have turned into the most anti-woman straight man on the planet. At the same time, she was simply the most evolved of any of the women I dated so I needed to be similarly evolved. I wasn’t at the beginning, and I never really got there while I was with her. Funny thing is I’m pretty close now - which is why I think she and I would get along great now if we’d never met before.

Maria

Actually Dated: 6th (My Age: 28-30)

There were certain things that just worked with Maria. There were certain things that just didn’t work with Maria. Whereas the problems with Nicole mainly stemmed from how we dealt with each other, the problems with Maria mainly stemmed from how we dealt with everything else. There was also the problem that neither of us really was the type of person that the other wanted to be with. Both of us tried hard to be that person, and it frustrated us to no end that the other person didn’t see our efforts.

Should Have Dated: 2nd

I think I needed a little experience to make it work, but that I had too much (if that makes any sense). She was relatively inexperienced, so I likely came in with expectations that she was never going to meet. Had we possibly met when we were the same age (she’s younger than I am so it’s not really feasible), we could have possibly grown together.

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Through this little exercise I learned something: there aren’t bad people (unless there’s some type of abuse going on) in dating, but there sure are bad times. Good timing is probably an underrated factor in finding a good (subjectively speaking) person. Interesting how that works.