I Tried Dating Multiple People At Once & Failed Epically

After ending a long-term relationship, I decided to take a stab at keeping my options open and dating multiple guys at once. This all happened over the course of about two months, and while at the “peak” I was seeing four guys at the same time, I made sure that each of them knew that we weren’t exclusive. If you can swing juggling multiple relationships (while being upfront about it), more power to you—I just couldn’t handle it.

  1. Having a “type” came back to bite me. I’m not talking about a physical type (though I do prefer brunettes), I’m talking personality type. What I learned is that the type of guy I’m drawn to meant being attracted to men who are usually in the business development/sales/marketing fields. That’s not all—when I dated multiple people at once, I unknowingly was seeing two men who were co-workers. This is not a drill. They actually discovered it themselves and then literally sent me a Snapchat of them together. I was mortified. We had an awkward laugh about it and then I promptly ran away.
  2. I started to bore myself. First and second dates always tend to cover the basics: where you work, where you’re from, and so on. I also have a set of entertaining stories that I pull out to get a good laugh. The thing is, after telling these stories time and time again to my various suitors, I just got bored. I’d forget which men I had already told stories to and they’d respond with various forms of, “Yeah, you told me…”
  3. My self-care went out the window. Juggling my own schedule is hard enough, let alone that of a significant other, LET ALONE that of multiple dates. I felt like I barely had enough time to get an adequate amount of sleep, and sleep is very important to me. Any time I did have to relax was interrupted by texting these guys—again, multiple at a time. Adding up all the time spent engaging in conversation felt like a second job.
  4. My skin is too sensitive to shave every other day. OK, this one is purely logistical. But with it being summer in the city, wearing jeans on dates was just not an option. It was a Catch-22: Either embrace the razor-burn and shave twice as often or show up to dates in a puddle of sweat.
  5. I 100% gained weight as a result of dating multiple people. When all this was going on, the vast majority of dates included food and drinks. We went out to dinner, went to food festivals, and saw movies. My calorie intake totally went up between the casual beers and fancy dinners, and I worked out way less often because I was so busy. Sure, I could’ve ordered the healthy choices, but I know myself, and if cheesy foods are an option I will never say no.
  6. I had to give them all nicknames. When filling my friends in on my latest romantic goings-on, naming each person got really confusing (especially when I was seeing two Matts). I resorted to describing the guys like they were episodes of “Friends.” There was The One From Miami, The One With the Pit Bull, The One Who Ran Marathons, and more. Not only was it challenging to keep my friends up to date on everyone, but it also started to feel really impersonal anytime I started talking about my dating life.
  7. I was always afraid of seeing them where I least expected it. Each time I was out with one guy, I was afraid I’d run into another. Even when I wasn’t with any of them, I felt a constant fear that I’d run into them. Even though it was highly unlikely, it felt like I had five romantic satellites roaming around and I never knew where they’d be or when.
  8. It felt like emotional whiplash. As I began to go on second and third dates, the dates all diverged and really started going at different paces. Going out with someone I really clicked with and then seeing another guy who hadn’t progressed as much was exhausting. The stress of it ended up affecting my mood and energy, and ultimately all the relationships ended.
  9. Read that again: All the relationships ended. Being involved with more than one person had so many negative effects—and that ultimately led to the demise of every single relationship. Over the course of a few weeks, all the relationships fizzled out. I ended the first few, and having the “I’m sorry, but I don’t see this going anywhere” conversation multiple times in a matter of weeks was terrible. To top it all off, the guy I really liked eventually ended things because “he didn’t feel like a priority.”
  10. I don’t know how contestants on The Bachelorette do it. Dating more than one guy at a time just left me feeling tired, guilty, and not myself. It took months for me to even have the desire to date again—and when I got back out there, I only put my focus on two people: a guy I liked, and myself.
Emily Boudin is a marketing professional based in New York City. She also is an active advocate for women's issues and shares about her experience with sexual assault and abuse.