The Most Unconventional First Dates I’ve Had . . .

Dating, at its most exciting, most memorable, is all about taking chances. That of course is easy to say and certainly harder to do. Despite that, not knowing the outcome of something, not knowing whether or not you will be rejected or left shaken is part of the deal if you fancy something potentially special.

By not having every detail planned, by breaking free of your comfort zone in regards not only to what you do on a date but who you date, you allow yourself the possibilities of new experiences and personal growth.

I support being unconventional and taking a chance (as I’ve often noted). It doesn’t mean things last forever or are without hardship or heartbreak, but why dwell on the negative when there is so much loveliness to explore? With that, allow me to share some (abridged) stories on times I (and she) decided to take a chance (of varying degrees) and said yes, making for a memorable first date.

The Double Date

This is the simple and lovely story of having two dates in the same day with the same person. After corresponding on one of those useful online dating apps, an afternoon meeting was arranged. We got along wonderfully, as coffee chatter turned into a lengthy walk and concluded in lovely fashion. We texted shortly thereafter to say some final remarks when I thought it worthy enough to ask why we shouldn’t meet up at night when we were free again—after all, the date concluded because of other engagements.

So we met some eight hours later. I opted out of my plans and we had more adult beverages while continuing our spontaneous dalliance.

The Result: Dating turned into a friendship, one that I was initially upset about but soon accepted and embraced, and that friendship continues to this day.

The Lesson: Take advantage of the time and opportunity before you, and don’t worry about playing games.

The Age Gap

I can hardly take full credit for this; maybe half. I was 22 at the time, and acted with reckless abandon and optimism trying to convince someone eight years older to give me a chance. We met randomly amid a lively street party, and I enjoyed a random night of drinks with random people I didn’t know.

That the first actual date happened was surprising. She was far more mature and sure about her life than I, and really, our meeting was fueled by drinks and excitement. I pursued, she relented, and despite the hesitation, we clicked, and more dates followed.

The Result: We were together for almost a year before ending the relationship. However we stayed connected and later became friends and built meaningful relationships from our meeting.

The Lesson: Don’t let convention keep you from taking a chance.

The Summer Whim

On a hot summer night, I waited for an hour at a dive bar for a date that never appeared. She didn’t have a proper phone (we were chatting via computer), and I guess it wasn’t meant to be. So I returned home, upon which I got a message from her: it took more than a few minutes to figure out we went to different places. Instead of calling it a wasted night, we decided to try again at a different bar, and I hopped back on my bike to ride some 35 minutes to a place I’ve never been to have an intimate drink well after midnight with a lovely writer I’d met online. It was a couple drinks, and a late night walk, some sparks, and a memorable night.

The Result: It was one and done, but well worth it. She wasn’t ready to proceed, but for me it was a worthwhile evening shared with someone new and exciting.

The Lesson: Dates are unpredictable, and there is always something positive to draw from them, however brief they are.

The Long Wait

While working at a cafe, I would see one woman every day, and I was taken with her since the first time I laid eyes on her. It took almost a year, after many casually suggestions and (sheepish) offerings of having a drink, but for some reason, somehow, one day, she agreed to hang out after work.

Even in that affirmative, I didn’t know if it was just us or colleagues in some social setting. No, it was just the two of us. We went for a long walk, to her place for a drink, then for another walk, then to a bar, and that all rolled into the morning. What was most striking were the conversations we had that kept the night going; there was so much we didn’t know about each other that we learning, despite saying hi and idly chatting for so long.

The Result: We dated for a year and have stayed in touch in each other’s lives many years later.

The Lesson: Be patient and allow for the right time to present itself.

The Road Trip

Warning: this should only be attempted by the most daring and ridiculous among us. This is the shortened story of how a Tinder correspondence turned into a four-day first date extravaganza. While on vacation some 400 plus miles from home, I sought someone to enjoy a drink with who wasn’t family. There was a match, but she wasn’t free; our timing was off.

A strange thing happened though after I left: we kept talking. Many, many messages and Skype chats later, we both agreed we reached a point where we really had to meet or else we’d drive ourselves crazy not knowing. The timing was such that the only way to do so was for her to drive nine hours to come and meet me, someone she had never seen in person, and hang out. Sure, it sounds super crazy (and it is) but we both talked about all the possibilities beforehand, agreed there was no pressure, and while it would double as a road trip and vacation to a new city for her, she always had the option of leaving whenever. Everything was above board and acknowledged.

The result: We got along in person too. We made sure we had our space, but movies and dinners and drinks and conversations made for a memorable, surprising, and indeed crazy first date. We spent four days and nights together, and didn’t hate each other after. We’ve stayed in touch and become friends since despite the distance.

The Lesson: Go visit strangers you meet online in other countries. I think.

Anthony Marcusa is a Toronto-based freelance journalist whose writing dabbles in film, TV, music, sports, and relationships – though not necessarily in that order. He’s simultaneously youthfully idealistic and curmudgeonly cynical. You can follow him on Twitter @MrAnthonyWrites.

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