Kate’s Dates: A retrospective of Valentine’s Days gone wrong

Kate's Dates Valentine's DayBy Kate Richlin-Zack

Valentine’s Day. Sigh.

In theory, it should be very romantic and fun and make you feel all warm and fuzzy inside.

Right. I can count on one hand the number of times that fantasy has EVEN COME CLOSE to reality. The most fun I ever had on Valentine’s Day—my husband’s efforts excluded—was making hideous jewelry with a bunch of my girlfriends and then getting drunk on tequila shots at the bar next door.

Having a date on February 14th does not guarantee a perfect night and, as you can probably imagine, I’ve had some pretty terrible Valentine’s Days.

I remember one Valentine’s Day when I was trapped in a relationship because I felt too guilty about hurting the guy to break up with him. I’d been planning to end things with Unemployable Kevin for a while, but every time I was about to sit him down because we need to talk, something awful would happen. First he lost his job.

Granted it was the fourth time he was fired in three months, so I really shouldn’t have let that stop me. But then his dog died suddenly and he was heartbroken … and Valentine’s Day was fast approaching. I didn’t want to be the heartless bitch that not only dumped him when his life was already turning to crap, but dumped him on Valentine’s Day. How cruel!

Because who wants to be alone on Valentine’s Day? That would be miserable, right?

Well, it ended up being miserable anyway. I had a pit in my stomach as we sat down for the lovely candlelit dinner he prepared, complete with wine pairings—he did spend a semester in culinary school. There was a fresh bouquet of roses and a bottle of expensive champagne. He topped it off with chocolate covered strawberries and a gorgeous bracelet. Perfect Valentine’s Day? Ha! Not even close. I was wracked with guilt. I didn’t want to be in this relationship in the first place, let alone spend a romantic evening with the guy. And how can anyone really enjoy a chocolate covered strawberry while they’re incessantly checking the clock and silently rehearsing, “But I have a headache,” and wondering what, if any, other tragedies in his near future might once again postpone the end of this god forsaken relationship? I mean, really?

In retrospect I would have been less of a heartless bitch if I’d just been honest and broken up with him before he took the time to orchestrate a perfect evening.

The following year, I still hadn’t learned my lesson. I had been dating Russell, The King of Inappropriate Comments for a few months.  Aside from the fact that he’d used multiple racial slurs the first time we had dinner with my parents, and the fact that none of my friends liked him, the sex was great … and Valentine’s Day was just around the corner!

I got a sexy new dress and he made reservations at a very romantic restaurant overlooking the beach. I promised myself that this year will be different! I didn’t think it could be worse.


When we arrived, the maitre d’ took my coat, and Russell gave me the once over. I was expecting, “Wow… you look amazing,” or something to that effect. Instead he said, “Oh… you’re wearing that?” I brushed it off.

We made our way through the claustrophobic restaurant to our table, nowhere near the alleged ocean view. We were practically in the kitchen and the table next to us was so close I kept bumping elbows with the woman next to me. I was struggling to maintain my cheery disposition, but I was determined. This year will be different!

We placed our orders and toasted to a happy Valentine’s Day with champagne. As I helped myself to some bread, Russell said, “I won’t say anything about you carbo loading tonight.”

Did he really just say that?

I was confused (and hungry), but I put the bread down. I was speechless and feeling incredibly self conscious. This year will be different, I insisted. I changed the subject and tried to make idle chit chat, even though I could tell the couple next to us was eavesdropping. Can you blame them? I’d be listening too, wondering what this idiot is going to say next!

Our dinner arrived and just as I was enjoying my first few bites, Russell said, “You should have them wrap up half your dinner so you won’t over eat. That dress is tight enough already.”

The man at the table just inches away nearly choked on his entrée and the woman gasped as she dropped her fork.  I gently put down my silverware and excused myself from the table. “What? Did I say something wrong?” Russell asked ignorantly as the woman next to me shot daggers at him.

I pretended not to hear him and tried to walk to the bathroom as quickly as humanly possible without making it seem like the place was on fire. I was practically hurdling over patrons in a futile attempt to keep it together. I burst into tears before I was even close to the ladies room, knocking over both people and things in my haste. It’s hard to see when your eyes are swollen with disappointment and shattered Valentine’s dreams!

I allowed myself a few minutes of crying, then splashed some water on my face. I wiped the streaks of mascara off my cheeks, and went back to the table. I didn’t think I had taken that long, but when I returned, half of my dinner was gone. GONE. Not because Russell asked them to wrap it up for me like he suggested, but because HE HAD EATEN IT.

Needless to say, I skipped dessert.

Despite those two truly terrible experiences, Valentine’s Day remains one of my favorite holidays. And I promise it can be one of your favorites too … if you do it right.

If you’re single, don’t spend Valentine’s Day alone. You’ll end up in your ratty pajamas, gorging on chocolate, downing whatever cheap red wine you have around the house because you’re too embarrassed to go out in public looking this way, watching whatever romantic comedy happens to be on TBS because you refuse to rent a movie because that would just solidify your pathetic solitude, and bawling because your life is nothing like what you see on TV. Not that I know from experience or anything. Instead, invite your friends over, put on your cutest pajamas, and encourage your friends to do the same. Buy a nice bottle of champagne, serve some classy hors d’ oeuvres, and don’t forget the chocolate. Skip the romantic comedy and opt for a horror movie. You can’t feel bad about yourself when you’re scared shitless.

If you’re in a relationship, I still recommend you stay home. Restaurants are overcrowded, the service will be terrible, and you’ll spend way too much money on subpar food. Instead, put on your sexiest pajamas, open up a nice bottle of champagne, and snuggle up on the couch. Serve some classy hors d’ oeuvres and don’t forget the chocolate. Skip the romantic comedy and make your own movie, if you catch my drift. You can’t feel bad about yourself when you’re the star of the show.

Kate’s Dates is a column that runs every other Wednesday on Kate-book.com. (It’s coming at you on Tuesday this week since, duh, it’s Valentine’s Day.) It is written by the lovely Kate Richlin-Zack, who you should follow on Twitter @K8RZ.

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6 thoughts on “Kate’s Dates: A retrospective of Valentine’s Days gone wrong

  1. Christine Yearing says:

    I think I may have been with you when we made jewelry and did shots…in red bank I think? That was fun times…

  2. plentyoffish dating
    Hi there! Would you mind if I share your website with my facebook group? There’s a lot of folks that I think would really appreciate your content. Please let me know. Cheers

    • katetorg says:

      Hey there plentyoffish. Of course you can share this column with your Facebook group. Just make sure to credit Kate Richlin-Zack as the author, and to link back here to the original on Kate-book.com.

      And check out more writing from Kate Richlin-Zack. She does this column every other week, and it’s always genius. Here’s more:


  3. [...] you meet his family.  Well, some of the aforementioned should never come out of your mouth period. The King of Inappropriate Comments was famous for this kind of stuff and it just made everyone uncomfortable. And he was ignorant [...]

  4. [...] be told, I love Valentine’s Day. I shouldn’t considering the crappy ones I’ve had in the past. But I [...]

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