I’ve always gravitated towards older friends. I was the kid on the playground who wanted to talk to the parents instead of playing soccer. I was also chubby, which may have had something to do with it.
Because I’ve spent most of my life trying to be older, as a general rule I always date older guys. (One time in high school I tried to date a younger one – it lasted a week. Too clingy.)
When I was in college, this wasn’t a huge issue. The older guys I was dating were still in their twenties and were typically lots of fun. As I’ve gotten older, though, the guys have too. With this lifestyle comes a particular set of challenges. If you’re going to date older, at least know what you’re getting into. Most older guys fit into specific categories. Here’s a quick guide…
1. The Man-Child
This guy is probably the most prevalent in my life. They are typically in their early to mid-thirties and just don’t know how to be adults. They have serious commitment issues because they never emotionally grew up past age 20. They seem fun, because – hey, no commitment – but there is a serious downside. They’re basically crazy. Date this guy if you want someone to break up with you in two weeks because you left a bag in his living room and he has space issues or some equally absurd problem.
2. The Workaholic
This guy is attractive because he has a stable lifestyle, which means he can pay for nice dinners and not force you to eat fast food for the week after. They work a lot, so they don’t like to go out much. If they do, they want to be home early, because hangovers are way worse as you get older, I’m told. And they worked all week and there are errands to run on the weekend. Or more work. Maybe date this guy if you’re a homebody and don’t like drinking too much.
3. The Narcissist
These guys are my favorite. In my experience, they tend to be a little older. Mid-thirties to 40 or so. I haven’t dated anyone older than 40, so they may actually go past that. I wouldn’t know. Anyway, these guys are the ones who seem so interesting in conversation, because they are, but afterward you realize you just had a three hour conversation and this guy probably didn’t ask you a single question. They are also typically pretty irresistible. Proceed with caution. You’ll waste a bunch of time never talking about yourself, but you probably won’t regret it.
4. The Jerk
This guy is still single because he’s just not fun to be around. I’m not sure he has a typical age range. He’s spent so much time avoiding serious relationships that he doesn’t really know how to treat people. He dates younger because older girls won’t put up with his antics. Do not date him. You will regret it.
5. The Family Guy
He has kids. He might be divorced or he might not. He probably talks about his kids a lot, but hopefully not in an annoying way. If you’re looking for more affection than you’d get from most dating older scenarios, this is probably the guy for you – these guys have kids, so they’re in touch with their feelings. Proceed if you’re looking for commitment and an insta-family.
6. The Divorcee
This one is tricky – depending on how freshly divorced he is, he can be a real mess. He can also be pretty commitment-phobic. But if you’re looking for casual, this guy is usually up for it. Because he’s not married anymore. He can do whatever he wants! Proceed if that’s your thing.
7. The Commitment Guy
This guy hasn’t been married and doesn’t have kids, but wants them yesterday. I date older because I have commitment issues and want to have fun with someone who has the same issues, so this is not the guy for me. If you’re ready to have a baby like, now, date him. You’ll be engaged within a year and probably married in two.
These are just my experiences, though. All I really know is even at their worst they’re way better than the guys my actual age.