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My Experience with “Serial Dating”

The university years are supposed to be a time of experimenting and self-discovery. But up until recently, I’ve been really bad at that. I always had this belief that relationships should be serious from the get-go and that I had to wait to find Mr. Right. I’d never been on a date with a stranger before this year, and I thought a date was a big deal. All this changed when I found myself mingling with five different guys – something called “serial dating”.

How it happened:

I met the first guy downtown one night. Sounds bad, but he was really sophisticated and gentleman-like. We didn’t talk too much that night and he wasn’t a big fan of texting (he believes that texting would ruin the mystery and would deplete the anticipation for the first date), so he was really a stranger to me. I was extremely nervous waiting for him to pick me up the first night; I was making up a million excuses not to go. But lo and behold, the date was actually amazing and I really enjoyed it, immediately anticipating the next time I’d see him.

Guy #2 is actually a good friend’s brother (which made things a little awkward at first). We met in December when he moved to Windsor to live with his sister in her new house. We got along instantly and became really close. When New Years rolled around, we admitted we had feelings for each other but were worried about ruining our friend group dynamic. Eventually we stopped caring (my friend’s didn’t mind that we liked each other) and got closer and closer. I was still going on dates with Guy #1 and couldn’t decide who I liked more. I had it in my mind that I had to settle down right away and I couldn’t make the decision.

Then the third guy came into the picture. He’s an old friend, so I already knew him but hadn’t seen him in a long while. It was fun to discover who we’ve both become and to just enjoy each other’s company without it being awkward. He lives about 2 hours away, so though he comes home often, I never really considered him a serious option for a relationship. I was just having fun and so was he.

The fourth guy was someone I talked to maybe twice before. I met him in a biology lab last semester and only worked with him on one lab. I followed him on Instagram when I saw him tagged in a mutual friend’s photo. After a few months – and actually while first talking to Guy #5 – I added him on Facebook and he messaged me half an hour after, quick to ask me out for coffee. I had no hesitation saying yes because I didn’t let my mind wander to the worst-case-scenario. I was genuinely interested and so I just said yes. The previous first date experiences lessened my nerves about going on this date.

Guy #5 was randomly suggested to me by a coworker. He brought him up in context of our conversation, but still kind of out-of-the-blue. I thought he was joking when he said we’d get along great and that he told him to add me on Facebook. But that night, I came home and saw the friend request (when I also added Guy #4). We had a nice conversation, but he didn’t ask me out till a week later. To be honest, I was smitten after the first date, and that’s when things started to change.


What I learned:


1.) My past isn’t as relevant as I once thought.

Because of my lack of experience, I didn’t really know what to talk about with Guy #1. I pre-planned before to talk about travelling (I’ve travelled around Europe, the Caribbean, and America) because it’s interesting and important to me. But that obviously didn’t take up the whole night. It took up maybe 10 minutes even though he’s an even more experienced traveller. He didn’t want to talk about the past; he didn’t see it as important as I did. Asking about childhood memories, where they grew up, or their former schooling is actually pretty lame. This might be obvious to you, HC readers, but I did not know. The person you are dating is living in the present, and so you have to focus on that.

This actually shaped the way I think a little. I always used to think that the past is relevant and that it still matters – it doesn’t. No one gives a shit about who you once were. They care about who you are now and what you do now. It inspired me to take more control of my present, to constantly learn new things so that I have more in my life to talk about – not just for the sake of interesting date conversations.

2.) I got pretty good at planning appropriate date outfits.

Especially first date outfits (as there weren’t always second dates). Coffee date with an artsy guy? Erie dinner date with an older man? Drinks downtown? Nailed it every time. It’s about genuinely being confident about what you wear. I know you’ve heard this before, but it’s true. You want to look nice and make a good first impression, but you have to learn to be real to your style and who you are; you can’t fake it forever. So if you like the sweater and it’s a casual date, wear it! Do your hair a way that feels good to you. Wear heels whenever you want – and never when you don’t want to. Enjoy makeup, but don’t feel obliged to put it on. At the end of the day, he’s dating you and he needs to know who that person is.


3.) It was originally a lesson for my friend, but it became a lesson for me.

My friend really liked one of my best guy friends but was too shy to ask him out. They didn’t talk too much and didn’t seem to share that much in common, so I understand the nervousness. But I wanted her to ask him out and to do it despite her fear to see what would happen. You can’t win the lottery without buying the ticket, right?

I figured if I could go out with the first guy, some random guy I met downtown, then she could ask my guy friend who she saw more than occasionally. I was so afraid before the date that I couldn’t feel my legs, couldn’t breathe right, and was getting hot flashes before he picked me up. (I played it off cool during the actual date, don’t worry.) Knowing how badly I was freaking out, my friend did actually get inspired to talk to the guy more. Though things didn’t end up working for her and the guy, at least I kind of fulfilled my goal.

But that wasn’t the main thing I learned. I conquered my own fears, which is so rewarding. Even though it’s something as simple as just going out with a guy, I combated my worst-case-scenario thinking and just went anyway. And, like I said, the date went really well! I became less nervous every time I met up with a new guy because I knew that most of my fears wouldn’t actually end up happening. I knew that it was all in my head and that it’s normal to feel nervous. But to experience things in life and to make great memories, you have to say “yes”, even to things you think are scary.


4.) How to “breakup” with a guy you’re not dating seriously

When things were going really well with Guy #5 (and yes, we’re exclusive now), I knew I had to somehow break things off with every other guy I was seeing. This was the hard part. I’m not good at saying “no” and I’m certainly not good with hurting people’s feelings. But honesty is the best policy, and I needed to be open with all of them. I didn’t necessarily say there was another guy (no one knew about the others and I didn’t feel it was okay to say “I’m choosing this guy over you”), but I gave closure to every one of them, letting them know where I stood with them. Don’t just stop texting them. Don’t treat them differently than before. The fact is, I still like the guys for who they are and I still regularly talk to a few of them as just friends. Just because you’re not romantically attached to someone doesn’t mean they can’t be a part of your life. Sometimes it can get awkward, but for most of the guys, it was a very understanding situation when I “broke up” with them. You won’t gain peace until you have that honest conversation, though.


5.) Gaining confidence and learning what I wanted out of the relationship

I gained a lot of confidence during this experience. It’s definitely an ego-boost to talk about the 5 (or more) guys you’re seeing with your girlfriends. Some of them ask you how you do it, making you feel like some goddess with super powers (which is definitely not the case; I’m an introverted English major who just happens to like good conversations and interesting men). But it goes beyond that. I didn’t worry so much about my makeup, my hair, or my clothes. I had fun playing it up for the dates, but that’s because I genuinely like those things. I wasn’t doing it for the guys. I figured if they had a problem with the way I dressed or looked, then that’s dumb and they’re not worth it. I knew from this experience that there actually are plenty of fish in the sea and that if one treats you even slightly poorly, then you have the right to cut him out of the picture instantly. Not worth your time. You’re better than a guy that treats you like you’re mediocre, and I finally learned that I am, too. The more guys you see, the more behaviours you learn about and the more experience you have figuring out what you like out of a guy and a relationship. I was so sure about Guy #5 because of serial dating. I knew what I liked and what I didn’t. It was a fairly easy decision to make.


6.) Girls can become pretty objectifying, too.

Warning: guys aren’t the only ones who can pretend a girl’s just a number. One weekend I was planning on going out with some friends. I don’t really like dancing with strangers, though, so I wanted to bring a guy I could dance and party with. I found myself texting one after the other. When one cancelled or decided he didn’t want to go, I knew there were others that could “take his place”. I’m ashamed of that now, and after a stupid text message to the wrong guy, I learned I couldn’t keep doing that. Treat people like people! Not numbers, and not options.


I’m not a promiscuous person; I didn’t sleep with these guys, but I was still judged by some for just dating them. I questioned my decisions pretty often, too. It’s very out of character for me to do something like this. To some of you this might seem like no big deal, but to me, this was opening up to strangers and learning more about who I am. I am definitely happier now that I’ve found one guy I can be comfortable with, but the dating experience (which took place over the course of a few months) was very exciting and flattering. Honestly, life’s short. I still believe in Mr. Right, but he’s not gonna propose to you out-of-the-blue. You have to open up to the opportunities life offers you for you to gain anything from them. And learning about people and trying new things is always a great thing. I hope one day you find Mr. or Mrs. Right, HC readers, but for now, live a little!

This is an anonymous account hosted by our team mascot, Mortie the Monkey. This article was written by a UWindsor student.
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