The Difference Five Years Makes While Dating In Your 20s

The Difference Five Years Makes While Dating In Your 20s

Before a recent encounter, I immaturely lumped people between the ages of 23 and 28 into the same category in terms of the way they live their life. In terms of the way they drink, go out to eat, behave, date and their overall mindset on dating. Being in the younger part of my own ignorant range showed me that my way of thinking is foolish and downright wrong. Yes, this is one experience but due to my insane narrow mindedness I will now base all of my assumptions on this going forward.

I recently came to this realization when I went on what was more-or-less a date with a 28-year-old woman. Let me add that I met her at a bar located in a popular summer weekend destination in the Jersey Shore. Let me also add that I had been drinking and may or may not have said I was 27 (I’m 24). Aside from navigating the conversation remembering that I had to tack on an extra three years to all of my life experiences, it was also enlightening. My findings are as follows (and as I run through them, quite obvious).

The places that people who are in their late 20s go out socially are much more expensive than the ones that me and my friends frequent. I requested, naively, that she pick the place. She ended up picking some rooftop bar by her place that had, like, $18 drinks. Tab was on me, as I am gentlemen. Three-ish hours of conversations and G&T’s add up to a pretty sizable tab when you’ve only been working one year, let me tell you.

The way they behave when on a date is vastly different. When I have gone out on dates with women (I use that term so, so, so, so loosely) my age, we didn’t get carried away with questions about where we see ourselves in five years, if we want to be at our current jobs forever or if our friends are getting married, etc. This line of small talk threw me off balance as I am an idiot who gives almost no thought to any decision I make. I also assume most dudes my age also don’t have this mindset.

Drinking in excess is also not an option. After our first drink, I suggested a shot to lighten the mood and she looked at me like I had four heads, giggled and politely declined. Proceeded to get a water and then another drink… I don’t need to explain how bizarre that was to me. I know the drinking slows down as we get older but again, it’s not what I’m used to so I figured it was worth mentioning.

The sense of urgency to get a significant other only ramps up with age while you are in your 20s. I am under the impression that we have plenty of time. Again, that is because I am 24 and use my parents age of marriage at 30 as a standard. BUT if you are in your late 20s, odds are you are seeing all of your friends get married/engaged and may go into subtle panic-mode. Now, it’s nothing that was outright said to me, it was the vibe of the whole conversation.

Essentially, all dates are like interviews but a date between two 23-year-olds has a vibe of “Okay, do I want to give this person another date?” Compare that with a date between a supposed (wink wink) 26-year-old and a 28-year-old who has the vibe of “Okay, is this guy mature enough to settle down for real?” Again, this is just one man’s opinion.

Women, no matter their age and until they find a boyfriend, will always claim it’s hard to meet dudes. How on God’s green earth is that even possible? For every girl at the bar, there likely are at least 7-100 dudes willing to at the very least speak to them. Now, is it someone they desire? Most likely not, but saying it’s hard to meet guys is absurd to me. You’re a girl, you have 100% of the entry power for conversations. Literally walk up to any dude anywhere and say hello I guarantee that he will respond back and attempt to have a conversation. It’s not for everyone but I wholeheartedly believe it.

All of this being said, I can truly say that I was lost and now have been found. Now, when I hit on a 27 or 28-year-old woman and they say, “Oh my God, you’re such a baby!” I will fully understand that they are telling me the truth. Relatively, I am an infant.

Because I, and most of my friends, am not nearly mature enough nor have enough money or mental capacity to pursue women in their late 20s, I am going to assume the same of every dude my age. It was a humbling experience and hopefully the above helps some other year-out-of-college moron who thinks it’s “cool” to date older women.

Email this to a friend

43 Comments You must log in to comment, or create an account

Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More