News & Politics

Dating Diaries Roundtable: Valentine’s Day

We asked our daters to share tales of their best and embarrassingly worst Valentine’s Day. Here’s what they told us.

Meet our datersDana Neill | Sally Colson Cline | Michael Amesquita | Kate Searby | Max Schwartz | Lucas Wall | Jenn Heilman   

Sally Colson Cline: “My best Valentine’s Day was in college. My mom sent me a pink-striped shirt that I still wear to this day. Also, any Valentine’s Day where I ate those little candy hearts ranks highly. I’ve never had a bad Valentine’s Day. People have bad Valentine’s Days when they have high expectations. I have no expectations. I don’t care about it very much.

“This is my first Valentine’s Day as a single woman, so I’m off the hook completely. There won’t be an 11th-hour grocery-store run to buy an obligatory wilted bouquet this year. Have pity for any girlfriends I might have in the future that put a lot of importance on Valentine’s Day, because I will sorely disappoint them.”

Max Schwartz: “I really have only been dating someone on Valentine’s Day, so I guess that means I have only one possibility for my best. It was with my first serious girlfriend in college, and because we were both new to living on our own and new to this kind of dating, we were both thinking—or at least I was—“What’s the big deal here?” I got her a pig stuffed animal–she liked pigs. I can’t remember what she got me. We went out to dinner. It was nice, though I don’t remember it really any more fondly than I remember the other dates that we went on. I’ve never really had a bad Valentine’s Day.

“It’s hard for me to see Valentine’s Day as a big deal. If you can’t be romantic in a non-Valentine’s Day situation, you probably have bigger problems than what to do on the day itself. And if you can, I’m not sure what makes Valentine’s Day so special.”

Dana Neil: “My best Valentine’s Day was a non-Valentine’s Day date. I had gone out with this guy one time. I didn’t feel like being alone on Valentine’s Day, but things certainly weren’t serious with him. So I called him up and asked him to go out to dinner. I reassured him there would be no strings and no expectations. I told him that he didn’t even have to buy me flowers. It would just be a fun dinner. We had the best time watching all the couples at dinner who were giving each other stuffed animals and chocolate and sentimental gifts. We were at an Italian restaurant with the red-and-white-checked tablecloths and the candle in the Chianti bottle, and they had tied red balloons to all the chairs. It was actually so sweet it was funny. It was a great night without any expectations.
“I really can’t remember a horrible Valentine’s Day. Maybe when I got caught up in it and made myself feel sad if I was alone. Maybe that was my worst.”

Michael Amesquita: “I don’t think I’ve ever had a special someone on Valentine’s Day, at least not for a very long time. I call February 14 ‘Singles Awareness Day.’ If you’re single, it’s the one day that you’re definitely aware of that fact.”




Jenn Heilman: “Is it possible for the best and worst Valentine’s Day to be the same one? The guy I had been dating for more than a year decided to set up a series of small surprises for me on Valentine’s Day. When I went to leave for work, there was a single rose and a thoughtful note waiting at the door. The inside of my car was covered with Post-It notes, and each had a reason about why he cared about me on it. Sitting on the car seat was a box of chocolates and another single rose and note. This note detailed three road intersections that I passed while driving to work where I found large heart-shaped posters dedicated to me hanging on street signs. At work, I found my last surprise: another rose and note with clues to our evening dinner plans. It was the first time someone had put so much thought into Valentine’s Day, but unfortunately he hadn’t slept the previous night trying to execute his plan. That made for a miserable evening when he got stuck in traffic, didn’t make our dinner reservations until after 9 PM, and then was too cranky to even talk to me or spend time together after dinner. I think that goes to show that simple can be better. It could have saved both of our sanity if we had decided to just spend quality time at home cooking dinner together or ordering a nice dinner to bring home.”

Lucas Wall: “My best was in 2001. The guy I was dating and I took a day trip to New York from Washington. We flew up early in the morning, did as much sightseeing as we could cram in during the day, and flew back at night. I don’t really have a worst Valentine’s Day. I’ve been single for nearly all of them, so I usually just try to let the day pass without thinking about it, as I’ll be doing again this year.”



Kate Searby: “My best Valentine’s Day was with my last boyfriend. He took me to some obscure play. It was terrible, but we had such a blast laughing about it together. Afterward, he cooked me an amazing gourmet dinner, and we spent the rest of the night sitting by the fire, talking and laughing. It was a beautiful night. As far as my worst Valentine’s Day, I haven’t had it yet.”



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