What Happened When I Broke All Of My Dating Rules

Full disclosure: I’ve been single for three years. Sure, I’ve dated like a hundred guys in that span (semi-relationships came from a handful of them), but not one of them has made it to serious boyfriend status. This, naturally, has led me to think all sorts of things about myself, especially when engagement 'grams are all over my feed. Is it my personality? Or my appearance? Am I hanging out in all the wrong places? Maybe I value my “me time” too much? Seriously, it's all crossed my mind, more than I'd like to admit. But that doesn't mean I've given up. I have, however, taken a bit of a break from the dating scene.

Over the last several months, dating has been my absolute last priority. Which I guess is crazy, considering I'm looking for the man of my dreams, and we all know I'm not just going to run into him on the street like all of those romantic comedies would suggest. Or am I? Nevertheless, I needed some time off the apps, which in a big city like mine is really the only way to meet a guy (weird, but true). I couldn't fathom spending another night in bed swiping left and right. I mean, who has the time — let alone the finger strength — for that? Plus, my workload was full-on, I had a Thursday-night dance-cardio class I wasn't about to skip, and my girlfriends and I had a big summer bucket list to get through.

But now that fall is in full swing, I'm ready to get back into my dating groove — is it just me or is there something about sweater weather that signals a new start? So two weeks ago, I went all in. I re-downloaded all the apps (Bumble, Raya, Hinge, you name it) and got to work. I vowed I'd line up a few meet-cutes and force myself out. Only this go-round, I wouldn't fall back into my typical first-date ways. What I failed to mention is that I've got the whole first-date thing down, too pat. I vet most guys before I right-swipe (true story), I order the same tequila cocktail, hell, I even wear the same outfit nine times out of 10. So instead, I challenged myself to mix things way up and break some of my major dating habits. Because, at the end of the day, if I don't put myself out there and take risks, I'm not going to find my match. So what happened? See for yourself, straight ahead.

I'll admit it. I love Google. Especially when it comes to dating. Here's the thing: I’m insanely scheduled. I value my friend dates and self-care way more than drinks with a random guy. So I never want to waste a night that I could be hanging out with a BFF or binging a reality show with a sheet mask on to get all dolled up to meet a guy I don't jive with. That said, scrolling through his Instagram feed or taking a peek at his LinkedIn profile gives me a little glimpse into his life — where he hangs out, what he does for a living, if he has good grammar, and so on — and is usually the deciding factor for whether or not I'll follow through. I know, I sound certifiably nuts, but I promise: I'm ready to put my old habits behind me. So for my first date, I banned myself from any and all internet stalking. It was a brutal few days leading up to the date, and walking into the bar knowing only his first name and his neighbourhood made me a tad uneasy. But guess what? It went well. Actually better than well. In a matter of minutes, I found out everything I'd ever discover on social media and more. Plus, it was kind of nice not having to pretend I didn't know his mom's first name for once.

Oh boy, do I have a type. I didn't think it was weird that every ex kind of looked the same, dressed the same, and basically had the same job until a girlfriend recently called me out. I don't know when I started to fall for the techy guy with glasses that appreciates a pricey pair of sneakers, but somewhere along the way, I did, and it stuck. This leads me to my second dare of the two-week span: to go out with someone that doesn't fit this mould, whatsoever. TBH, my plan was to give a colleague free reign on one of my apps, but I chickened out. I did, however, match with someone different than my typical type (he worked at a hedge fund and had an affinity for boat shoes, which was obvious from his photos) and secure a date. He picked a bar I wasn't really sure about. I love a cozy spot that veers more low-key, and his suggestion was one of those fancier restaurants finance guys flock to once the market closes. Don't worry, I rolled with it — as the new me would. I hate to say it (because wouldn't it be totally amazing if he turned out to be the one?), but the date didn't last very long. We didn't have much in common, aside from both being spin-class regulars, so after just one drink, we got up and said our goodbyes.

Remember when I said I was scheduled? Well, here's the deal. I hate to stay out late on a weeknight — even when the date is going well. Why? Because I value my beauty rest and my job requires a whole lot of brainpower (as in, hangovers don't fly). Sure, I used to stay out well past sunrise in my early 20s, but I'm an adult now, and I've got shit to do. That said, in an effort to conquer by biggest dating fears, I vowed to let loose and have a little fun again on my next date — pending I didn't have a huge project due the morning after. Now by this, I don't mean I wanted to be Uber-ing home at 4 a.m., but I reminded myself that I wouldn't be losing any glass slippers at midnight. When I made a plan with a guy midweek, I was fully ready to stay out later than usual, assuming we hit it off. I ran home after work, refreshed my eye makeup, and slowly drank an espresso while I added a few more waves to my hair. I felt energised and ready to go wherever the night took me. We met at a chic speakeasy, and a few drinks in, I suggested we bar hop — which we did, for another four hours. My drink-to-water ratio was on point — it only took me 10 years to get that down — so I wasn't, well, freaking out about a potential hangover. I made it home just a few hours before I'd usually be waking up (I'm an early riser), slept for a few hours, and started my day. Talk about living my best life.

A few years ago, I had a sober first date that was just downright awkward. We met up on a street corner, and he took me shopping — for a men's cologne. We got vegan food and never saw each other again. Now look, I'm not a big drinker whatsoever. But having a cocktail in my hand (preferably a tequila one) takes the stress out of trying to decide whether or not the guy I met 20 minutes prior is partner material. Not to mention, it helps sort out my butterflies, takes the edge off — you get it. But I know I've got to be open to no-drink dates, too. So I finally gave into one of those guys that asks to meet on a Sunday. I was nervous, of course. I never know what to wear on a day date. The lighting is different. Head-to-toe black (my go-to) can feel a bit morbid to some men. Do I wear sneakers? Mini-heels? I still haven't quite mastered it, and I work in fashion. But I manned up and met a guy that actually lived in my hood at a trendy coffee shop around the block. I didn't feel as comfortable as I would have had I sipped on a glass of vino beforehand, that's for sure, but 10 minutes in I realised it wasn't as bad as I had made it out to be in my head. We took our second round of coffees to go and walked around — still sans alcohol. I couldn't believe it. I was on a day date, and I was into it. Looking back, there was something refreshing about being totally on my A-game, especially for someone completely type-A, like me. And of course, remembering everything.

I bet you want to know what happened with the four guys, right? Well, as of right this very second, I'm still talking to one of them — the guy whose Instagram feed I didn't stalk. We've been on a few dates and have another one on the books for next week. So who knows? He could be the one or he could not be. Either way, this whole self-challenge thing really gave me a new outlook. Let's be real: Dating is no easy feat. It can diminish your self-confidence. It can wear you down. But it can also be empowering. Sure, I went on all of these dates because I had a story to write — but also because I was ready and willing to throw myself back into the ring and take risks. And because I did, today, I'm happy to report that I am more confident than ever that he's out there (just as long as I keep the "stalking" at bay).