Kat’s Adventures in Dating: Valentine’s Day Edition

I do not hide the fact that I think Valentine’s Day is the best. I know, it’s an unpopular opinion. Whatever. 

The one thing about Valentine’s Day that can suck for everyone is ambiguity. If you’re just sort of dating someone or in a situationship, it can be hard to determine expectations or boundaries. I really appreciate bravery and trying, and I respect people who put themselves out there even if they’re not sure what the response is going to be – not just on Valentine’s Day, but in life. It’s worth it, I think. 

So I thought I’d share some really excellent Valentines that missed the mark – not because they didn’t try, but because I wasn’t in the same place they were.

I Choo Choo Choose You

Matt and I had been seeing each other for about a month when Valentine’s Day rolled around. He was a chatty, exuberant, bearded, outdoorsy type – a skier and mountain biker who at least knew about the Mountain west where I was from. He was also an enthusiastic eater and loved going out to dinner. Basically, he was always hungry. 

The feeling I remember from our time together is him talking and me quietly going about my business. It wasn’t that he wasn’t interested in me – I’m sure he asked questions and listened thoughtfully to my responses. He just had a lot to say, all the time. 

I had just gotten out of my first real long-term relationship and I was a hot mess. I was not ready for a relationship with anyone, honestly, and dating was a distraction for me so I wouldn’t be sad about that breakup. I tried to be straightforward with partners about this, and I was sure Matt understood, although looking back, I’m guessing my 26-year-old self was a lot less clear than I thought I was being. 

To be perfectly honest, the only thing we really had in common was coffee. I had worked as a barista for several years and he really liked coffee. It probably contributed to his chatty exuberance – he was basically always hopped up on caffeine. I made coffee for him when he came over, and he really enjoyed that. How easy that is, in its simplicity. 

Valentine’s Day was coming up on a Saturday, and because it was really my first time being single in several years, I had decided to devote the holiday to my friends. I spent the weekend before the holiday painting watercolor cards for my best girlfriends and my sisters. I lovingly addressed the homemade Valentine cards and sent them on their ways.

On the Friday before Valentine’s Day, Matt showed up at my door with a huge bouquet of roses and a box of drugstore chocolates that included a picture of a train and the slogan “I choo choo choose you” on the front. (Anyone who loves the Simpsons will get this reference.) He also had a very thoughtful card that featured a black and white photo of a latte on the front and probably some verbiage along the lines of “I like you a latte” and included some very heartfelt words he had written inside.

I was flabbergasted. I had nothing for him. I thanked him profusely, of course, but I truly had no idea he (or anyone else, for that matter) was planning to do anything for me for Valentine’s Day that year. 

Verdict: Honestly, I basically ghosted him (I was young, sorry). I started seeing someone else more seriously the following month and just quit texting him, although I did eventually tell him (via text, casually, like a true coward) that I was seeing someone else. 

Kermit the Frog as a Cupid

I met Josh on Tinder back before it was a complete dumpster fire. We agreed to meet for coffee (I was trying NOT to meet for drinks for a change) and I was very charmed by him. He was a captain in the fire department, which meant he was pretty fit. He was also very funny and sweet, which was a bit of a surprise. 

During our hour-long initial meeting we both disclosed that we counted gift giving as one of our love languages. He really enjoyed listening to a date and figuring out what they might like, and getting it for them, before they knew they needed it. That was one of my favorite things to do, too. 

We went on a second date, this time to dinner and wine at a nice restaurant. We had a good time, from what I remember. Conversation was easy, he was cute, respectful, polite, interesting, funny, and interested. Josh was genuinely a really good guy.

But again: I had just gotten out of a long-term, serious relationship. And I wasn’t in a good place for a relationship. I was dating multiple people and not settling on anything. I was very casual with everyone. 

When Valentine’s Day rolled around that year, Josh surprised me by leaving a package on my porch. It included:

  • A small yellow Moleskine notebook, because he knew I liked to write, and he knew yellow was my favorite color (after two dates!)
  • A pen, but not just any pen – his favorite pen, which he knew would write well because he used the same brand all the time, exclusively
  • A drawing of Kermit the Frog as Cupid, because he knew I liked the Muppets (and he was a really good sketch artist)
  • A single flower, because he knew I liked them, but he didn’t want to go overboard

I sent pictures of everything to all my girlfriends. What a sweet, thoughtful, amazing gesture.

And what a terrible person I felt that I couldn’t return it.

I’d tried to get him a little gift – some lip balm, because I’d thought his lips had been chapped – but I never got around to giving it to him. And his lips weren’t chapped at all; he took really good care of himself, including wearing chapstick. (Another element that added to his charm – he seemed like a real adult.) 

Verdict: We kept in touch, and he even captained a team in my adult kickball league, but we never went on another date. According to his Facebook (since we’re still friends on there), he is happily married to a beautiful woman with a gorgeous child, and I couldn’t be happier for him.

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