Tips For Dating An Older Dude

Sometimes my friends joke to me that my life is like a movie, and sometimes they’re right.

It was a casual Wednesday afternoon and I was taking my weekly trip to Trader Joe’s. I love the dirty hipster look, so I always joke with my friends about how I’m gonna meet my husband at Trader Joe’s. Unfortunately the joke is usually on me because I end up standing in line next to an older Indian man asking if I want to get coffee sometime..


However, this time was different. I was nearing the end of my shopping trip when I went to grab some green tea. The guy standing next to me happened to be sexy as Hell, but I tried to play it cool and ignore him. Suddenly he asks me if I’ve ever tried the diet sodas here (nice line, I know) which eventually turned into a coffee date after we had finished up with our groceries.

Keith was the type of guy that makes my jaw drop. Slicked back hair, covered in tattoos, green eyes, and a small nose ring. He was also 30, making him ten years older than me. We had a lot of fun while it lasted, but there were a couple things I wish I had known before getting involved with him.

DO: Be pleasantly surprised at his assertiveness and planning skills.

How refreshing it was to be seeing a guy who planned dates ahead of time, called me to discuss details, and knew exactly when to make a move. There’s something to be said about calling rather than texting, taking the extra effort to call a chick makes you seem so much more together. The fact that he took me to a banging Japanese place and a speak-easy bar in Chinatown after? Bonus points.


DON’T Describe every stupid detail of your life on the first date.

Although Keith obviously knew that I was much younger than him, I did my best to not spend my time on our first date talking about things like the frat parties I attend on the weekends. At a later point in our relationship I obviously didn’t hold reservations, but I didn’t want to make him feel older than necessary on a first date.


DON’T Expect him to be the best you ever had.

Being 10 years older than me, I equated that to ten more years of sex that he’s had. At dinner one night we laughed about the fact that when I was four years old he was losing his virginity. But, sex the first time with Keith wasn’t mind-blowing or earth-shattering by any means, it was just average.


DO: Tell him what you like.

While the first time wasn’t incredible, Keith was quick to pick up on the type of things I am into sexually, which I loved. As we got to know each other better and became more comfortable, we tried things I had always wanted to try that he had already done before, which was awesome.


DO: Leave your party girl alter ego at home.

When Keith and I went out to dinner, we usually drank a decent amount as well. I made sure to follow his drinking habits, because as a college girl I have quite the tolerance and am usually enjoying (or chugging) boxed Franzia rather than sipping a glass of Pinot Noir. When he brought me to a BBQ at his friends place, I tried my best to fit in. It did get a little weird when his friend’s three year old daughter kept asking me how old I was…


DON’T: Try to bring him around your friends.

Keith was cool and he seemed young, when I was with him on campus my friend even asked if he went to school with us. However, I still refrained from bringing him out with me and my friends, that was a whole different level of ratchet that I didn’t need him to see. When I did bring him to my place the first time, it was a Thursday night and my roommates were downstairs pounding shots in preparation for going out later. He tried his best to fit in, even taking a hit from my friend’s blunt, but it still felt very strange to me.


Ultimately, while Keith was a fun experience, I think at a certain point we both realized that we were both at drastically different stages in our lives. While Keith was more mature than most guys my age, this was a good thing in terms of boyfriend material, but a bad thing in terms of my social life. Ultimately, he showed he wasn’t any different in the way that things ended. The other girl that he had been seeing showed up at his house when we were supposed to hangout and gave him an ultimatum; and he chose her. Can’t have your cake and eat it too sweetie, even when you’re 30.

Gimme More Dating

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