The Sweet, Strange Mystery of a First Date


The Sweet, Strange Mystery of a First Date – Wit & Delight

A year or two ago, I arrived for a first date at a quiet cocktail lounge to find that every table was taken. My date met me at the door, scanned the venue a few times, and finally turned to me. “Okay… I guess we can sit at the bar—as long we don’t sound like we’re on a first date. Deal?”

Uh, okay?

By date three it was clear this guy was consistently more concerned with how he looked than making a real connection, but I do somewhat get his point.

There’s no date like a first date

On a regular basis, I’ll be sitting behind my laptop screen at a coffee shop, trying not to eavesdrop on the first date happening next to me, which is difficult when the tables are eight inches apart. I’ll tell myself, “You don’t know for suuure it’s a first date.”

But I do. There are just certain kinds of questions—and a certain way those questions are asked, usually starting with the word “So.” (So, where do you live? So, do you ski? So, you’re an accountant?) There’s also a certain kind of giggle and a high usage of words like, “Oh, really?” and “That’s cool.” It can be awkward to overhear, but there’s a freshness to the conversation. People are in a heightened state of curiosity. They seem to be existing in a conversation bubble—the world around them barely exists. Spoken and unspoken questions are being answered. There’s a buzz of possibility, risk, and mystery.

A first date has a particular nonchalant intensity that rarely happens in other settings.

I’m an unintentional expert

I know this because I’ve been on a few (dozen) first dates. More than I ever thought I would, that’s for sure. Pre-marriage, I had approximately four first dates: one each with my junior high boyfriend, my high school boyfriend, my college boyfriend, and the guy I married, with maybe one or two others sprinkled in. And most of those could hardly be called dates. They were basically holding hands during a slow skate and never letting go.

But I’ve been divorced a long while now, and I’ve learned a thing or two about the kind of first dates that involve dressing up and sitting down with a beverage and a man I’ve never met.

The Sweet, Strange Mystery of a First Date – Wit & Delight

Maybe I’m odd

Some people I know get sweaty palms just thinking about first dates. My married friends often express relief that they’re past that phase, “especially these days,” with online dating and social media redefining the experience. One friend can’t wait to get to the third date, because that’s when she feels like she can finally be herself.

Perhaps I’m strange, but I like first dates. I like meeting someone new, going somewhere new, asking questions, answering questions, and laughing a bit (sometimes in my own head). I like the feeling of possibility. I like hearing someone’s story and sharing a bit of my own. And, of course, I don’t mind walking away with a few great stories to share.

Oh, the stories

There was the guy who was 10 years older and 20 pounds heavier than his dating-site pictures. The waitress had to help me find him. He didn’t look bad – he just wasn’t the same person I had been conversing with online. He was unrecognizable. I felt duped.

Another guy, based on his online profile pictures, was either going for a hipster-ironic-nerd aesthetic or he actually owned a pocket protector. I couldn’t tell for sure. He was smart and funny in his emails, so I agreed to meet up. But he was so overwhelmed in person that one minute he was making blunderingly inappropriate comments about my appearance and the next he was in tears as he described tender memories of his ex-wife. (I do believe he owned at least one pocket protector, but that wasn’t really the issue.)

Then there was the guy who, minutes into our fish-and-chips lunch—our first conversation of any kind—declared that he was done looking and was ready to start a relationship with me. An hour later, he had texted me an apology for the awkward goodbye hug beside my car (as I was trying to get away), with a link to the music video “I Should Have Kissed You.”

The Sweet, Strange Mystery of a First Date – Wit & Delight

To judge or not to judge?

It’s hard not to judge people on a first date. Then again, I guess maybe that’s the point? For me, a first date is somewhat of a relationship interview. Or, at least, it’s a tryout for a second date. If I am buying a new house or choosing an avocado or hiring a housecleaner, I am certainly incredibly judgy. Knowing what I’m looking for, and what I’m not, is critical to the process.

But I’m also so aware that we are each more than the first-impression version of ourselves. I know I am—and I hope I can judge, and be judged, with that in mind. People are not houses or avocados, and they should be evaluated with care and nuance. And kindness.

Also, at my age, there is a bittersweetness to first dates. Behind the smile lines and the thinning hair on the other side of the table is often a family that’s been broken. A heart, for sure. And, except for a few players I’ve encountered along the way, most guys have taken a risk to be there with me. I appreciate that, and I may laugh at the details or say no to a second date, but I don’t dismiss a good person.

The beautiful unknown

There’s something about a first date that is pure, raw potential. Will a connection be made? A friendship? Sparks? Will this be the moment we each remember for the rest of our lives? Or will it be just another coffee shared on a Saturday afternoon? Will we both leave this meeting feeling the same, or will one of us have our hopes raised, only to see them dashed?

There are definitely things about my married friends’ lives I hope to once again enjoy (the comfortable familiarity of a long-term relationship, for one) but, for this season of life, it’s been a beautiful adventure to embrace the mystery and potential of first dates, face to face with the brave men who are doing the same.

Image sources: 1 / Images 2 / 3 Photography & Creative Direction by

BY Julie Rybarczyk - January 10, 2018

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I really liked this post! I’ve been with my boyfriend for over six years now so I don’t really know what a “first date” feels like anymore. This makes me feel so nostalgic!

Charmaine Ng | Architecture & Lifestyle Blog

January 10, 2018 4:48 pm

I love this Julie! I’ve been with my husband for about 13 years and though I don’t have any real experience with first dates, I’m a little sad that I haven’t gone on many. It seems like such a fresh slate, and at the same time, I really enjoy meeting new people. I also enjoy the story of the people I meet, who they are, what challenges they face, it always feels like opening a bit of a present.

January 10, 2018 6:58 pm

I’m still young, haven’t been in a serious relationship and first dates don’t have the same air to them as they do for you yet. But your comment on not dismissing the person is so important. Loved this read <3 Thanks Julie!

January 11, 2018 9:31 pm

At 60 years old, I am contemplating dipping my toes back into dating. I was married for 35 years, and have now been single for 6. It seems so scary and daunting but even my kids are telling me it’s time.The problem is I haven’t met anyone who even seems like someone I would date, or else everyone is married. Should I sign up for Match?? This is what everyone says I should do, and just weed through the bad ones until I find my prince lol. Anyway, I really enjoyed reading your post, it gave me a lot to… Read more »

January 12, 2018 10:02 am
Reply to  Patricia

Go for it, Patricia! And report back. 🙂

January 12, 2018 11:32 am
Reply to  Patricia

I agree with Amy! I say go for it, Patricia!!

January 12, 2018 11:34 am

As with all of your other pieces, Julie, I so enjoyed reading this one. In fact, it inspired me to recreate my first date with my husband! Sometimes life can get so hectic and we can forget how precious sweet moments like meeting someone for the first time can be. Thank you for this reminder.

PS – I LOVE your idea of first dates with friends!!

Dominique Williams
April 22, 2018 7:47 am

I so enjoyed this piece. I went on a first date last night and had an admirable time. It began raining at the end but he was a true gentleman and ran to get the car so I wouldn’t get wet. Does the rain signify anything on first dates? At the end of the dinner he stated, “I have one last question, would you like to do this again”. Needless to say, I smiled and said of course.

Cheers to the POSSIBILITIES!

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