We asked: Have you ever gone on a first date on Valentine’s Day? Errr, that sounds like there’s some potential for an awkward situation. Have you ever been broken up with on Valentine’s Day? Yikes, we don’t want to hear that!
Well, except that we do.
Like we said, we put the questions out there, and boy, did our readers and viewers deliver. (Pssst: There’s still time to answer, if you’d like to participate!) ⬇️
Anyway, we gathered up nine of our favorite responses involving Feb. 14, from people who are able to look back and laugh. Here they are! (Answers, in some cases, have been edited for clarity, length and grammar).
“I met this guy, he asked me out for Valentine’s Day, we went to a free dog show — romantic, right? — but I was cool with it, because I do like animals. But then we saw my aunt and grandma there, and he insisted on hanging out with them the entire time. Then he asked me to drive him to the store. When we went in, he grabbed a teddy bear, fake flowers and some groceries, we got to the check-out line and he asked me to pay for it because he forgot his money. And then he handed me the plastic bag with the fake flowers and bear, and said, ‘Here you go. Happy Valentine’s Day!’ Most romantic date ever. **insert eye roll** ”
— Jamie from Roanoke, Virginia
“Way back in my 20s, I found out the man I was engaged to … was married!”
— Rose from San Antonio
“My mother’s birthday is on Valentines Day. When she and my dad starting dating, they were both living in Toronto, Ontario, in Canada. … They had a date planned to celebrate mom’s birthday. Dad was a couple hours late, which made mom pretty angry. When he finally arrived, she told him as much from the top of the stairs to her flat. He responded by saying that he had something for her. Her response was, ‘Throw it up here.’ So he did. It was an engagement ring. They married in Niagara Falls in September 1952. The reception overlooked the falls. They were married for 60 years.”
— Evelyn from Troy, Michigan
“I made a date with a woman for Valentine’s Day, 54 years ago. I spent every last dime I had for this date. I showed up at her apartment only to find another man there, playing a guitar and singing. She and her three roommates were all sitting around in casual clothes. When I arrived in my suit and saw what was going on, I asked her if we actually had a date. The dude left, she ran upstairs and changed while I waited, and became madder and madder. We did complete our date and were married for 52 years before she passed away a year ago last October.”
— Jerry from Wimberley, Texas
“Once, in the early years of marriage, my then-husband and I wanted to eat at our favorite restaurant on Valentine’s Day. The wait was two hours for a table for two. The hostess asked if we would share a table for four with another couple — we could get in faster. So we did! We had dinner with a young couple. It was so awkward! We made idle chit-chat, exchanged business cards, and then never spoke to them again! At least we got our dinner in decent amount of time.”
— Jeanie from Houston
“My first day in divorce court was on Valentine’s Day.”
— Paul from Saint Cloud, Florida
“This isn’t a ‘funny’ love story, but I feel it’s unique in connection with how our lives repeatedly had crossed paths, beginning in being raised (in the 1940s) a mile or two apart in the Brooklyn / Queens area of New York City. Many times, even into our teens, we were in the same place at the same time. We finally met the day before freshman orientation at Hope College, Holland, Michigan. And ‘this girl’ sitting next to me turns and says, ‘I know you.’ We got married four years later, in 1960.”
— Ronald from Christiansburg, Virginia
“In 1999, I was talking to a man I had known eight years before, in high school. We had gone to coffee a few weeks before, but plans kept getting canceled. We finally decided to go out on Valentine’s Day for our first date. Valentine’s Day is also my birthday, and I had told him that a few times on the days leading to the holiday. I agonized on what to bring. Should I bring a card? A gift? Nothing? I settled on a small inspirational book and bookmark — friendly, but not too much. He met me at the restaurant with … absolutely nothing. Not even a card. He seemed not at all perturbed that he had made such a glaring faux pas.
I should mention that exactly one year later, we landed in Ireland for the first day of our honeymoon. He has been showering me with gifts on the week of my birthday (which includes our anniversary on Feb. 12) every year since. This will be our 21st year of him making up that first birthday/Valentine’s Day date.”
— Valencia from Jacksonville, Florida
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“It was our first Valentine’s Day together in 1994. In 1992, Hurricane Andrew had destroyed the Japanese restaurant Samurai, and it was under construction for a long while. Every time we would pass by the restaurant, my girlfriend then would say, ‘I’m dying to eat there.’ Well, Valentine’s Day 1994 came around, so I figured it would be a great place for Valentine’s Day. I excitedly made the dinner reservations knowing she was ‘dying to eat there.’ Guess what? After dinner, she was not happy, and said, ‘That is not a restaurant for Valentine’s Day.’ Jump forward to 2020. We have been married since 1995, and since Valentine’s Day 1994, I have not made another dinner reservation. I now let her handle that part of our relationship. We laugh about it all the time.”
— Manny from Miami