Dating in your 30’s is weird. You’re stuck in the middle of guys who are in their late twenties still living with their parents or room mates and trying to figure out what to do with their lives, and 40-something men who are likely already divorced and have kids, but who are searching for someone to be with for the second half of their lives. On top of that the 30-something men are a mixed bag. Some are ready to settle down. Some are still acting like they are twenty and partying on weeknights. Most of them (at least the ones I seem to interact with) are not really sure what they want. I’ll also add that most of them are your typical millennial in that they want attention and admiration but they don’t want to put in much effort. Like is asking a girl out on a date and planning something really that hard? I’d almost rather have fun and hang out with 20 something guy because at least then I don’t expect as much from them as far as life direction, achievements and knowing what they want. When I go out with a guy in his 30’s and I subconsciously expect him to be on the same level and same page as me. I guess that is where I am going wrong. I have been TRYING (unsuccessfully) to date men in their 30’s for the last 4 + years.
And in those past few years of dating trying to find “the one”, I’ve on both ends of the cougar/prey spectrum. I know you’re probably thinking, how did I become a cougar at 31? Wasn’t I supposed to have a few kids and a failed marriage or two before that happened? Sheesh! Well I started my online dating journey when I was 27 and now at 31 I have somehow become a cougar. I get messages all the time from 26 year olds saying “I’ve always wanted to be with an older woman.” I wasn’t mentally prepared for this that’s for sure. Do those guys really think I am going to be flattered by being called an “older woman”? Bad choice of intros.
At one point I just went with it and was seeing a 23 year old when I was 30. At first I was thinking it was weird, and I just about spit up my froyo when told me he had literally just turned 23 (as if 23 ¾ years would have been somehow more socially acceptable). However then I thought about how I had recently dated a 41 year old when I was 29 (12 year age gap), so screw it! It can most definitely go both ways. But in general men take a bit longer to grow up and most of them, even at 30+ are just hairy, big kids, so I do think it is a little more challenging for women to date downward in terms of age. But, dating a younger guy can be fun. Kind of makes you feel like you have some of your youth back. I remember making out in the car after picking him up from his parents’ house and thinking “wow I haven’t done this since high school”. And you can also teach the younger ones a few things if you know what I mean (ahem cough cough). But when the goal is something long term and settling down I feel like that’s hard to achieve with a younger guy because they just aren’t ready for that. Thus the term “boy toy” I guess. They are something to have fun with and but it won’t last for the long haul. My little fling with the 23 year old ended after I was over him still talking to his college sweetheart and being indecisive about what he wanted. I told him I don’t share.
And now for some failed attempts to lure in the cougar (me):
Buddy, you are literally 3 years younger than me! Grrr…..
Gosh I hope I don’t have the cougar look already. I am going to go buy some anti-wrinkle cream and maybe even start wearing sunscreen.
And then there are the older men. There is something really attractive about a grown ass man, having lived his life and who knows what he wants and will tell you. Having online dated for a while and gone out with a few older men (think 8 year age gap +) I can say it is so refreshing to have someone ask you out… take you to dinner and make plans and take initiative. Stark difference from the flaky men my age or younger who can’t even seem to commit to when or where to meet up and would rather have a texting pen pall for weeks on end only for you never to really meet up in person. This might be a generalization and sure there are exceptions but for the most part this is what is wrong with dating at 30. So much indecisiveness, flakiness, men not knowing what they want and wanting to play games until they figure it out. All at the expense of us 30 something quality women who are so ready for the next step of building a future with someone and commitment. That’s probably why a lot of women do try dating an older man at one point or another. It’s fun. They treat you with respect . And it is sort of fun to be an older guy’s hot piece of ass and eye candy that he can show off to his friends. Sorry mom.
Sure there are some awkward age gap moments. I’m thinking back to watching Top Gun with an ex of mine who was 12 years older (and really good looking in case he is reading) and him saying “This came out in ’86. I remember because I had my first kiss watching this movie”. To which I replied “Hm… I was 1”. Then we both stared at each other for a second obviously both thinking “is this wrong?”. The other problem with dating an older man is that they might already have kids and not want to have more kids, or be at an age where they don’t want to have kids because they feel like it’s too late and they don’t want to be that older dad. But if given the choice I would definitely chose older. Just looking for that diamond in the rough I suppose who either has kids and is willing to have more or who hasn’t had any yet and is willing to take the plunge later in life.
I suppose I should enjoy my early 30’s as a time where I can both pick up my boy toy at his parents’ house for a froyo date and also be wined and dined by an older man. Trying to look at the positive of being extremely single at 31.
P.S. No young boys were harmed in the content gathering for this post. I did however almost kill a 40 year old man on a workout date to Thousand Steps Beach in Laguna during which he could not keep up. Warning: Not all 40-something men are created equal.