theres a first for everything

Dating Tips

Written by AdminAugust 3 ,2016825 Views single parent dating

Quick question for the peanut gallery: would you go on a first date on Valentine’s Day?

On the one hand:

  • All the restaurants and bars in New York City are already dressed up for capital R Romance with pink and red balloons, paper hearts, and dinner specials
  • The version we celebrate in modern times is so far removed from its early Christian and Pagan origin as to make the current iteration of V-Day effectively a consumer free-for-all.
  • At least you’re not spending a holiday focused on love and couples alone and by yourself

And yet, it still gave me pause when Maxwell from Match asked me out for Saturday night, February 14th. It’s kind of weird, right? But I couldn’t put my finger on why, exactly.

It’s not like I’m a huge Valentine’s Day person – I don’t really celebrate at all, in fact. I think one year I went to see a Nicholas Sparks movie with my roommate; another year I bought a bag of reduced-price chocolates. I love chocolate. That’s probably the extent of my participation.  By that token, it was really any other night, albeit one with outside expectations.

So I said “yes.”

What to Wear on a First Date on Valentines Day

Since I wasn’t coming straight from work, I had a brief brain-freeze trying to figure out what I should wear. I couldn’t exactly wear what I’d been wearing the whole day (black checkered pajama pants, grey sweater). Wearing pink or red would be a little too on the nose, and while I might appreciate the absurdity, I didn’t know my date well enough to gauge if he would take my look seriously or not.

I also considered wearing a dress, because in addition to the holiday mood, Maxwell from Match was an international type living in New York and I wanted to impress on our first date. Yet, in the end the streets of Manhattan disagreed with any and all of my plans, and I had to settle on jeans and snow boots, again, so I didn’t get a foot-full of slush or contract hypothermia when I left my apartment. Oh well…

Recognizing Your Online Date – A Guide

Stage 1: Consult his online profile

Maxwell only had one picture on his profile, so I had an idea of what he looked like, but when I showed up at the hotel bar I didn’t see anyone who looked remotely like the dude on my phone smiling and wearing a winter hat.

In case of emergency, proceed to Stage 2: enlist help

According to Yelp, which I consulted beforehand, this bar was a hotspot for first dates, so I turned to the hostess in my time of need.

“I’m supposed to meet someone here?” I trailed off, hoping I would find him soon. “It’s, um, a first date so I’m not positive what he looks like in person.” I felt incredibly lame. She gave me a conspiratorial look and indicated towards a few single guys sitting by themselves by the bar and then assured me there was an exit by the bathroom, in case things went poorly, quickly.

Clearly, she was on my side. Finally, Maxwell walked over from the table he’d snagged in the corner and we had contact! Score!

A Date of Many Firsts

I had a few other “first times” while on this date:

The first time… my date ordered a second glass of wine after I had declined a second round.

The first time… my date visited the bathroom twice during the two hours we sat getting to know each other.

The first time…I went on an online date with someone who didn’t grow up in the United States

The first time… I had been at this hotel bar

The first time… someone has ever given me a convenience store chocolate rose because we were meeting up on the same day as the Holiday of Romance. Yes, he brought me a chocolate flower, which was incredibly sweet.

Addendum: A Tip for Getting Out of an Online Dating Funk

I sometimes like to pretend Patti Stanger from Millionaire Matchmaker is giving me a pep talk before I head out on a date. She’s the kind of woman who talks straight, and once in a while if I’m feeling out of sorts before having to put my best foot forward I imagine her saying in her sing-songy New Jersey accent “look at you, you’re adorable! You have a real job, you went to a fancy school, why haven’t you been snatched up yet? It’s crazy!”

If you’re ever feeling a little overwhelmed/underwhelmed with online dating, just listen to the imaginary Patti on your shoulder. She’s always, right, anyway.