I Went On 10 Tinder Dates Over The Holidays & It Led To The Most Unexpected Relationship


When my two-and-a-half year relationship with my partner ended, I immediately bounced back with a whirlwind relationship. Just one problem: my ex and I were still living together. When my live-in ex moved out the same day my new guy moved back to San Francisco, I took six weeks of much-needed "me time." And when I was finally ready to dip my toes back into the dating world, I went on 10 Tinder dates over the holidays.

I wasn’t looking for a relationship at the time, because I’d been through all that and then some, but I was looking to get out of the house, meet new people, and get back on the merry-go-round of dating around. And it just so happened to be the most festive time of the year. Giddy up!

I re-downloaded Tinder, the app I met San Francisco Dude on (and had deleted after we became a thing). It worked with him, so I figured why not give it another go? It was like the holiday catalog I never knew I wanted. I used Tinder like an advent calendar, going on dates with different dudes every night.

One night, I met up with my match at The Dakota Tavern, my favorite live music venue in Toronto. As he got us a round of drinks, I couldn’t help but look around and noticed a long-haired, bearded guy making magic up on stage as he played his pedal-steel guitar. As my date tried to chat me up, I tuned him out to tune into the guy on stage. I was smitten. There were 10 musicians up on stage, but he held my attention for the rest of the set.

I allowed my date to drop me off at home, then woke up early to do "research." I emailed the venue to find out the name of the band, then looked them up online and read each member's bio to figure out the mystery musician's name. Once I did, I changed my Facebook settings so a few of my better-looking pictures were on "public," and sent him a friend request. He accepted it immediately. I messaged him to say I couldn’t help but notice him at his gig the other evening, and point-blank asked if he was single.

After going on so many dates in a row, I had learned that men weren't intimidated by confidence — they were drawn to it. And I had learned that you can't get what you want unless you ask for it. Music Man was flattered by my message, told me he was single, and we wrote back and forth to each other all day. He even invited me to his next gig, which happened to fall on New Year's Eve.

I debated if accepting his offer and hanging out with him for the first time on New Year's was too much. But I love live music, enjoyed his band's vibe, and didn't have my heart set on going to a fancy party with fair-weather friends. So at 11:15 p.m., I bid adieu to my girlfriends I was out with, and went to go see about a boy.

I spotted him the minute I walked into the venue; he's 6'6", so that's not a tough feat. He noticed me right away, grabbed us a round, and we had our first conversation IRL. As we were chatting, the countdown begun and when it struck midnight, he leaned in for our first kiss. It was so unexpected but felt so natural. For the next 15 months, we had a casual relationship, which was just what the doctor ordered.

We bonded over our love for live music, and I became close with his fellow bandmates, attending their shows every Sunday night. We both had some short-stint random relationships throughout that time, but always ended up back together.

Our relationship — or whatever you want to call a no-strings attached bond between two people who admire, respect and connect with each other — was perfect for me at that time in my life. There was no pressure and we both enjoyed our independence. We were on the same page. And I never would have worked up the courage to track him down if that string of Tinder dates hadn't put me in the right state of mind.

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