Here’s Why Your First Date Should Never Be On Valentine’s Day — Trust Me, I Tried It

Valentine’s Day might seem like a cute, romantic option for a first date. That’s what I thought when a guy I’d been getting to know on a dating app invited me out for V-day dinner. Little did I know that it would totally kill the romance. Here’s what happened.

  1. Roses are red and I was anxious as hell. I usually feel nervous before a first date, but going to meet a guy I was chatting to online for a few weeks on freaking Valentine’s Day really increased the pressure. I worried that he’d expect more out of the date because of the romance in the air.
  2. He brought me a rose. The cliché to end all clichés: the guy brought me a red rose from “the guy who was selling them in the parking lot.” Great. He really shouldn’t have because he made it seem like he was going through the motions of what society expects on February 14 and I was not with it.
  3. The restaurant was straight out of a rom-com. There were loads of couples everywhere. There was romantic music playing and stupid heart-shaped decorations all over. Ugh. It was like Valentine’s Day puked all over the place. It’s really hard to focus on getting to know someone in a casual way when there are people sticking tongues into each other’s mouths everywhere you turn.
  4. The day brought attention to how we weren’t a match. On the dating app where we’d “met,” we were a really good match. In real life, seated in that romantic restaurant, we just didn’t have much to say to each other. Awkward! Under normal circumstances, this would’ve been uncomfortable enough, but it was made even more so by the fact that we were in such a lovey-dovey place. Ugh.
  5. I felt desperate. I was the one who chose the restaurant, albeit without knowing it was going to be so romantic. Now, in his eyes, I probably looked desperate to have someone and find the love of my life, especially because I really dressed up for the date. Ugh.
  6. I should have stayed at home. Truthfully, I was a bit lonely and anxious about being on my own on the most romantic day of the year. So when he’d suggested meeting up in person, it was a relief. I ended up wishing I had just sucked up my stupid feelings and made an excuse. I could’ve avoided this awkward situation.
  7. The waiter wouldn’t let it go. The waiter kept referring to us as a couple and we both seemed to be too embarrassed to point out that we were on a first date. But I cringed every time it happened, especially because I could see that we’d never go out again and my date was cringing just as hard as I was.
  8. I tried to lighten the mood and it backfired. I could see he was feeling as nervous and awkward as I was, so I decided to approach the purple elephant in the room. “Don’t worry, it’s not like I want to marry you or anything just because it’s Valentine’s Day,” I said with a laugh. Instead of laughing along, he just glared at me. Did he think I’d dissed him or something?
  9. I tried to make conversation. I didn’t want him to think I was sarcastic or mean so I tried to make friendly conversation. What had been his best Valentine’s Day ever? I thought that would be a fun question.
  10. He wasn’t over his ex. He told me the best V-day he’d ever had was when his previous girlfriend had surprised him with a romantic day. They were supposed to have been getting married on this very day. Uh, TMI much? He then launched into a conversation about how crappy it was when she dumped him completely out of the blue. He clearly wasn’t over her. Ah, that explained his touchiness when I’d cracked a joke about not wanting to get married to him.
  11. The pressure intensified. After dinner, I started hinting that I wanted to get the bill, but we couldn’t because the waiter insisted we get dessert. They had a special red velvet cheesecake on offer, like we cared. However, we both decided to go for it, and having to sit through the dessert while my date went on and on about how love was pain was too much to handle. I couldn’t wait to finish my dessert and get out of there! Luckily, he didn’t insist on walking me to my car but he did expect a kiss. WTF? Too many desperate people do the rounds on this day of the year. I’ll never have a first date on Valentine’s Day again!
  12. It made the bad date a hundred times worse. Leaving a bad first date that doesn’t go as planned always makes me feel a little empty. But leaving this Valentine’s Day date was the worst. Being surrounded by so many happy couples highlighted for me how much I hated not having someone special in my life. But it made me feel unnecessarily morbid. Ugh. I’ve definitely learned my lesson. From now on, Valentine’s Day is banned from my dating calendar. I’m going to snuggle up with my cats instead.
Giulia Simolo is a writer from Johannesburg, South Africa with a degree in English Language and Literature. She has been working as a journalist for more than a decade, writing for sites including AskMen, Native Interiors, and Live Eco. You can find out more about her on Facebook and LinkedIn, or follow her on Twitter @GiuliaSimolo.