Listen, I don’t know what I did to deserve bad karma in my dating life, but it looks like it’s here to stay, and I’ve finally come to terms with that. I was going through a bad breakup with someone I had been dating about a year. My friends and I had gone to a new bar near my friend’s apartment to check it out and indulge in some drinks. I was getting a lot better mentally, if I had been asked to go out a few weeks prior I would’ve said no, I was so upset over the breakup. But I was learning to be happier again and being with my friends helped to cheer me up and distract me. The last thing I expected during the worst breakup of my life (so far – let’s be real here there will probably be more), was to meet someone who really changed my perspective on dating and even on myself. 

I went up to the bar to order my friend and I drinks and started chatting with these two guys sitting at the bar. I brushed them off to talk to the bartender, asking his advice on a drink, when I noticed his Grateful Dead shirt. Let me just say I know that it is way more typical to see someone in a Grateful Dead shirt in San Francisco (their birthplace), but with the tech bro takeover, it hasn’t been as easy anymore. And I love the Grateful Dead, thanks to my father who introduced me to them. My dad and I would take little road trips together jamming out to the Dead, so they have a place in my heart. 

“Oh my god! I love the Dead. Have you seen them as the Dead and Co?” I asked the bartender. 

“No, actually this is my dads’ shirt, I haven’t listened to them too much,” he replied. My heart sank a little honestly. 

I can’t remember my exact words, but I know I teased him for wearing a band shirt that he doesn’t actually listen to. We both laughed and I returned to my friends, not thinking much about the conversation. My friends and I continued drinking and hanging out at our table, the bartender coming over once to bring us water (rare, am I right), and then telling us he would give us all free shots if we went to sit at the bar. Naturally, we did, and we ended up talking and having a really good time. 

I’m a little oblivious sometimes, not really noticing that he was mostly talking to just me until my friends pointed it out. It was getting late, so we decided to leave the bar and get some food. I got the check (which was definitely reduced) and tipped the bartender generously. This was when it got more interesting – my friends and I were standing outside the bar so they could smoke, and we were talking about how he was clearly interested in me and I should go get his number.

Making the first move is difficult enough for me already, as I can be pretty shy with that stuff. But since I was still recovering from a breakup, it was even harder for me so I literally hid outside while my friends angrily went back inside to give the bartender my number (I was scared! Don’t judge me). 

The next day, I get a text from him asking me to hang out. I said yes, much to my surprise, and we made plans to get coffee and to go to the mall. A couple of hours before the hangout, I called my mom sobbing. I hadn’t gone on a date in so long and I wasn’t sure if I was ready.

But I went and had a good time. We made plans to go on a real date the next day, and that was fun too. We got along really well and liked the same things. And the most refreshing thing about him was that he knows what he wants in life, he’s settled down and is very comfortable in who he is.

This isn’t shade against guys I’ve dated my age – because I’m going through the same thing of being a little lost in what I want to do with my life, it’s just part of being in your early twenties. But I’m a very ambitious individual, so while I have different ideas every day on what to do with my life, I still have the same main goals for myself. So I really liked this about him, that he had already done the hardest part about growing up and had his set goals.

The bartender and I didn’t last for more than maybe a month. I did like him there’s no doubt about that, but I was still in love with my ex. My ex and I got back together, and that’s something I don’t regret. I think we had a hard breakup because we both knew we needed some time to ourselves but still wanted to be together. We connect well and I liked that we were growing up together in a way. We graduated from college only a week apart and we’ve both been going through the same struggles of starting out our careers after college. 

Dating someone your age is great for that reason because you go through new experiences together and you know that the other person can relate. And while someone older than you has already gone through it and can give advice, it’s different because a partner closer to your age will understand the emotions better as they feel them too.

There are pros and cons to dating people from any ages and I think that should be the most important thing taken from this article. And everyone’s dating experiences are their own, and not anyone else’s. For me personally, I don’t mind if my partner is my age or 10 years older. Being with someone my age is fun and supportive in a deeper, emotional way. Dating someone older than me put things in perspective for me – because he was comfortable with himself, he had set goals in life, and knew what he wanted; it really inspired me to start doing that for myself as well.

I’m a big believer in that we meet people for a reason: to teach us lessons. Even if they fall out of our lives, or have a negative influence, whatever the case we still learn from them. And sometimes, these lessons prove extremely valuable. And guys my age can be mature, just like guys 10 or more years older than me can be immature.

2 thoughts

  1. I enjoyed reading this! This part really stood out to me:

    “Dating someone your age is great for that reason because you go through new experiences together and you know that the other person can relate. And while someone older than you has already gone through it and can give advice, it’s different because a partner closer to your age will understand the emotions better as they feel them too.”

    My boyfriend is younger than me so I consciously strive to ensure that I give him that space to make his mistakes, to be young and carefree. Sometimes our thinking diverges because of our experiences but I do agree there are perks of dating someone your age and someone with a difference.


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