I Dated Five Guys Simultaneously & I Learned So Much

Juggling even one relationship can be a challenge, but what about five of them? As it turns out, it’s possible and chock full of fun life lessons. Here’s what I learned from dating five dudes at once.

Discovering open relationships changed my life. In my early twenties, I discovered polyamory along with the rest of the millennial population, it seems. Suddenly recognizing that love and sex don’t have to be coupled with possessiveness and jealousy, I set off to explore all the possibilities that now lay before me. It totally changed my view of romantic and sexual connections.

I love forming connections with different people. Falling in love is one the greatest experiences of life, so why not do that over and over again? I love discovering new people and seeing what comes up in an as-yet-unknown dynamic. Developing a spark with someone unexpected is one of the things that keeps life interesting and having the opportunity to form that connection, even if I’m already in a relationship, is something I’m not going to pass up.

Each partner added something different to my life. Every guy I was with during this time was completely unique from the others. One was an analytically-minded engineer and taught me to think logically and rationally. One was a playful, dread-headed hippy, introducing me to a culture of love and acceptance. One was a tantric masseur and together we expanded our understanding of sexuality. Another was a writer and helped spur on my passion for the written word. The last was a mix of spiritual enlightenment and street smarts with whom I could share deep conversations with one minute and grind my booty with the next.

It was a juggling act sometimes. With five different dudes to keep track of, it sometimes became a challenge to keep all my affairs in order. At some point, there just aren’t enough hours in a day to spend quality time with each of them, spend time alone, hold down a job, and maintain other friendships too. Occasionally one would suffer while I tended to the others, but in the end, I somehow managed to balance everything. It made me appreciate how important good planning and good communication are.

I found different parts of myself came out with each lover. Because each of them was so unique, I got to discover different facets of my personality depending on who I was spending time with. This hugely stretched my understanding of myself and helped me access interests, skills, and beliefs that I might not have discovered otherwise. I’m a much more well-rounded person for that experience and I’m grateful to have crossed paths with such inspiring individuals.

Some relationships tended to overlap despite my best intentions. As much as I’d like to be able to keep relationships separate, the fact of the matter is that everything is interconnected, especially when it comes to relationships. As much as I tried, I couldn’t stop myself from making comparisons between my respective partners. This is a weird position to be in and I always felt a little guilty about it.

Comparisons were sometimes good, sometimes bad. I don’t think comparisons are necessarily a bad thing. In some cases, it actually really helped other relationships. The things I learned and experienced with the tantric masseur greatly improved my sex life with the writer, for example. That said, sometimes it worked the other way. My connection with the writer was much deeper than the one with the masseur (which was more of an FWB arrangement) and I eventually put an end to the latter to make more room for the former.

Each relationship ran its course. Not all of these relationships lasted the same amount of time of course—that would be weird. Each of them had their own nuances and their own ups and downs. The overlap between all of them was a hectic and fascinating time, but eventually, they scaled themselves back naturally. Most of those relationships ended organically, simply because the connection was no longer there or because life circumstances got in the way.

There’s no ‘one-size-fits-all’ for relationships. One of the greatest lessons I learned from this experience was that every connection is different. I never tried to make any of these relationships fit into a mold. Instead, I was able to experience each one on its own terms. In a monogamous relationship, it can be tempting to make that person fit what a relationship is “supposed” to look like. Here, I was able to just roll with it and see what developed by itself.

It helped me appreciate each connection for what it was. Because I wasn’t looking for a happily-ever-after, I felt free to experience each connection for what it was. The tantric masseur wasn’t boyfriend material but he was an excellent lover, and I could be very happy just keeping it on that level. The hippy traveled extensively so our relationship didn’t fulfill my needs for contact but then, it didn’t need to. The writer was a great short-term relationship but I didn’t see us spending our lives together, but it was still valuable for what it was. I really learned to let go of expectations when it comes to relationships and I think anyone, monogamous or not, could benefit from doing the same.

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