I am going to psychoanalyze myself a little. In college I was an aspiring ladies’ man. I never had consistent luck; I was too aloof, too arrogant, too into the party to really invest in any relationship; not that women were knocking down my door anyhow. Those that were into me, for whatever reason, I typically blew off, treated poorly, or turned into ephemeral specters of my life. I was immature then, and to some degree still am. While I look back on my undergrad years with great fondness, the one area I could have improved upon would definitely have been the romantic relationships (as in beyond a one-night stand). This takes maturity, wisdom, respect – for others and oneself – and for some of us (me), it came slowly. Therefore, it goes without saying that there was even less interaction with the opposite sex in high school. In some ways I think that is where I learned my hard edge, especially since some of my first encounters didn’t go in an ideal fashion (as I’ve written elsewhere). So I started my life of romantic pursuits on a hard luck story and evolved into a callous caretaker of others’ feelings. It has taken a while to shake that arrogance and disregard for others’ feelings, but I’ve finally turned the ship around (I think).

So it seems that these days at damn near 40 I’m still stuck in my 20s, at least romantically. I think this is so based on my last 4 relationships, and another one previously that was my longest. When I was 29 I started dating a 21-year-old, and did so for about three years. That isn’t that big of an age gap, really, but at least noticeable. At 36 I dated another 21-year-old; much bigger age gap. That lasted for maybe three months, but as we were in different states, that isn’t surprising. At 37 I dated a 26-year-old for about six weeks; I had already made plans to move so that isn’t surprising to have ended either. At 38 I dated a 21-year-old for a few months before I moved again (see Always Leaving, Pt. I & II in this series for more on this). Now, at 39, I have recently met a 22-year-old; who knows what will come of that. Too early to tell. Now, the odd thing is all four approached me in one way or another, so it isn’t as if I’m out stalking younger ladies. But it is curious to me that so many years later when I’ve finally found a groove, and an interest, that the ones I begin seeing are so much younger. It has to have something to do with my stunted relationship development from high school to college, right?

The old folks’ home never sounded so good.

When I tell my 40ish friends about the younger gals I’ve been dating, they are often envious. Most are married with kids, so they find a little vicariousness in hearing about my tales; I guess it takes them back to college. Most of them had far greater success than I in the relationship department back then. What is also of interest to me is that I was aware of their talents in this area; I was the one who was jealous years ago. As much as I shot myself in the foot and acted like a jerk back then, I did want to find a real and lasting relationship in some capacity. I think. I know I had unrealistic expectations, I know I didn’t take advantage of the opportunities presented to me. I know that the karmic wrecking ball knocked me over to save others of having to deal with my BS. But nevertheless, I did always pine for some connection way back when.

When I moved from my home state out west for the first time, then bounced around the country for several years, I never found any consistency or grounding in my life. Especially not in dating. So I think over the years I was more defined by other things and the “other” person never came into play much; or at least not for very long. But somehow, as time wore on, and my snakeskin of juvenile foolishness slowly shed from my fiber, I started to look for those connections. I must have put out some signal of what my relationship maturity level was – twentysomething. Fortunately, I look a lot younger than I am; I am often told that I could pass for 10-12 years younger so seeing my “29” year-old self with a 22-year-old probably isn’t that off-putting. But I do wonder what people think when I say I have been largely dating girls close to have my age in some cases. It makes me quiver a bit. I can only imagine what traditionalists and the more conservative think. I’ll assume that it is I need to grow up, to put it lightly. Certainly to stay away from their daughters, too.

When I think about how I would “design” the perfect girlfriend, she certainly wouldn’t be 17 years younger than me, though I do prefer the girls I date to be younger, at least by 5 years or so. Why? I’m sure part of it has something to do with them being “preserved” longer. I know, sounds terrible. Maybe I really haven’t matured much… I also think that many women look for older guys; maybe not 17 years older, but a few years. Why is that? I imagine it actually does have to do with maturity levels to some degree; women, for the most part, mature much quicker than guys. Or at least I think they do. I’m trying to recall the last lady I dated that was within a few years of me. For a short month not too long ago I dated someone that was 5 years my junior. That fell apart for a number of reasons, but a big one was that she was way too “clingy.” Maybe that measured up to some stereotype I have of dating “older” women; that they’re trying to settle down ASAP, and I’m not, really. With younger gals I don’t have to worry about that. These days if you’re 22, “settling down” should be the farthest thing from your mind. Right?

In the end I don’t know what to think. I know I’m not the most mature person in general, and I’m sure I’m stunted in numerous areas. I think that if I’d had an appropriate role model to show me how to engage with romantic interests, maybe I’d be looking for something different today. But instead I never really learned the proper way to go about these things, and because of this, I go back to the period of my life when I went full off the tracks – college. I’m trying to rebuild my romantic life one young lady at a time, slowly learning how to be a mature adult in a relationship with someone who is at my “dating-level.” So, casual bystander, judger of other men’s souls, I am not a creep. I am not trying to corrupt young ladies’ hearts. I’m simply trying to find someone to match mine. It just so happens that they more often than not seem to be younger – by a lot. But as I stated, they’ve been coming to me. So I must exude something. A youthful spirit, a playful smile, a willingness to try to learn romantic life at their level. If I were to date a fortysomething instead, would I find someone just like me? Wouldn’t it be that much more difficult? More than likely they’d have had their fair share of stunted romantic development, too. So should I look for another pea from the same pod, or is it okay for me to catch someone on their romantic upswing, perhaps before they’ve been completely jaded? As long as I’ve reconciled myself with my issues, and don’t let them affect someone else, regardless of age, can’t I be twentysomething again in the dating world?

Marco Esquandoles
Young at Heart