Well, another Valentine’s Day and another February have come and gone — possibly our nation’s most polarizing holiday in our nation’s most hated month. At the very least, it’s a fickle season. “Love comforteth like sunshine after rain,” said the Bard. But he also said, “Love is a devil” and a “madness … [that] deserves as well a dark house and a whip as madmen do.” In any case, through all of its miseries and elations and gentle comforts, the human heart soldiers on year after year, grateful, most days, for the gift of romantic love. With that, here are just a few of our best and/or worst (first) date experiences.
Best: We were newlyweds living in snowy NYC for our first Valentine’s Day. I had foolishly decided to wear high heels, and despite the fact that the restaurant was three blocks away, my husband insisted we get a cab. When we pulled up to the beautiful, windowed, corner French cafe there was a huge snowbank between where the cab had stopped and the sidewalk. My husband got out of the car, walked around, picked me up, carried me over the sidewalk. And the people in the restaurant clapped. – Sarah Condon
Worst: My parents would not let me go on a date until I was sixteen, and then I had my very worst one first. He took me to Cracker Barrel for dinner, and as an activity, we walked around an abandoned hotel in Jackson Mississippi. He insisted we find our way to the top so we could get a view of the city. Once we got up there, he looked at me and told me he was having a diabetic low and asked if I carried any candy. That man is still not married, to no one’s surprise. – Sarah Condon
Best/worst: It was the best of dates; it was the worst of dates… Actually, it started off a fiasco. We sat down in the pizza/brewery and the server tripped and spilled beer down the left side of my body. Juliette and I weren’t sure what to do but kept our cool and figured I’d dry off. Then the cup began to runneth over. They provided me with a free shirt, comped our meal, and gave us dessert. Just before we were going to leave, the server asked which tequila I preferred because the godfather-looking-gentleman and his wife at a nearby table were impressed with how we didn’t berate the server and wanted to take a shot with me! The date did not go according to plan, but it’s an all-time great in our shared memory. – Ryan Alvey
Best: It was just supposed to be a half-hour coffee date. Two and a half hours later we were still talking. Talking, talking, talking. With astonishing ease, we both found all manner of secrets and personal intimacies and family quirks kept tumbling out of our mouths. I can’t speak for my (now) wife (of five years), but I think I knew, whether I admitted to myself or not, this one was going to stick. – Ben Self
Best: I met a girl at a Las Vegas nightclub while grooving alone on the dance floor, inebriated by a different type of spirit, when a friend of hers pushed her into me. After some mumbled speech, we found out we lived right by each other. Back at home I took her to drinks, dinner, and arcade games where, upon presenting our IDs to the bartender, my great Vegas lie was exposed. I was only 23 when I’d told her I was 25 (advice my older brother gave me since his theory was women like older guys). Funny enough, it turned out I was actually younger than her, but she wasn’t too upset — although I must say my brother was proven right as she confessed to texting her friends “He’s 25!” after we had initially met. Now, I’m 32, honest to God, and we’re married with two kids. Maybe what we mean for evil, God means for good. I think I read that somewhere. – Blake Nail
Best (…?): The year was 2002. White capri pants and Goo Goo Dolls were in. I was serving my first ever jury duty, in which the plaintiff, a young man from Westpoint, was desperately seeking money for sustained injuries. By the end of the week, I had done no help in granting this wish. Lawyer dues and court fees in one hand and his phone number in the other, he took one more swing at opportunity. He complimented me on my eyes, while I clammed up and took that little paper with his number, blushed, and walked out of the courthouse. Over the span of one week, I ghosted him, assuming I was in the clear, only to find the kindest, handwritten letter waiting for me in my mailbox, wanting to get to know me.
“Wait, you didn’t tell him you already have a boyfriend??”
“No, I was just gonna ignore him!” (Warning to boyfriend: she has confrontation issues.)
“Janell, you have to call and tell him.”
Realizing that it was pretty sad it was my boyfriend telling me this, my sheltered ego picked up the phone and called the number. With relief, I heard the voice of his mother on the other end. (Oh, thank God!) Being the grown-ass woman that I was, I took the opportunity and explained to his mother why I could not date her son. A few days later, I received an apologetic note with two symphony tickets. Whether or not this was a pure chivalrous act or a last-ditch effort at proving his worthiness of a callback, we may never know … But that’s how Avoidance 101 got my future husband and I our first date to the symphony. – Janell Downing
Best: My first clue that she liked me was how unusually excited she seemed when I happened to stop by her place of work. We were in the same Bible study but rarely spoke to each other. Even after pulling me over the shop counter and kissing me like I’d never been kissed hello before, I was still a little slow on the uptake. Putting it down to cultural differences — she was from Ipanema, after all — I thought she was being really friendly (crazy, I know). The penny finally dropped when she invited me to stand with her while she was being baptized. Our church baptized in the ocean, and it was then I suddenly realized; this was a date. Not only that, it was a first date with a sacrament! It certainly put a lot of pressure on the second date: Would I need to perform a minor miracle? Turn water into a nice Pinot Grigio? After four years together, the grinding poverty of my pseudo-calling didn’t prove to be the romantic catnip I had hoped for in a long-term relationship. Made for a helluva first date, though. – Josh Retterer
Best: This is definitely not a “first” date … In fact, it was after my husband and I were married and had a couple of kids. But every once in a while, when one of us does something embarrassing or the food we’re eating is really messy, we like to joke, “What if this was our first date?” At this time in our lives, going on any kind of date was rare because we lived in Hawaii without any family nearby and literally had no money. But on this occasion, my mother-in-law was in town and watched the kids. So, we went to be extras in a movie. A romantic walk on the beach in Honolulu AND getting to act like we’re running away from a ballistic missile? AND getting paid for it? Best date ever. – Juliette Alvey
Worst: For some strange reason, one time I agreed to a blind date with an acquaintance’s nephew. We went to dinner and a movie. I tried to find something in common … He was in the Air Force, so I told him about my cousin who is in the Air Force and how he just got promoted to … I couldn’t remember, maybe Colonel? A guess which got me immediately laughed at. You would have thought I just said my cousin was the President of the United States. Looking up the Air Force ranks later, I understood why he laughed in my face, but still. The whole evening passed without him asking one thing about me (no exaggeration) while I scrambled for things to talk about. And then, I kid you not, literally a block away from my house at the end of the night he says, “So what kinds of things do you like to do?” – Juliette Alvey
Best: A few years ago, I spent a few weeks on the dating app Hinge to reenter the dating scene after a breakup. I had low expectations, but thought I’d at least emerge with a few funny stories. I went on a dozen or so first dates with a funny variety of Hinge folk, but one stood apart from them all. I met my date one afternoon at a botanical garden in my town, where we would walk among the flora, find a bench and get lost in conversation. After about three hours of this, we agreed to get some dinner. Four more hours later, we stood in the parking lot and I asked if he wanted to see me again. Nearly four years after that, we are celebrating our second wedding anniversary and expecting our first child together! – Kate Wartak
Worst: At a new job, some female coworkers warned me about a man who was on the hunt for a wife. He’d asked out nearly every girl who worked there, to no success. My policy has been to always say yes to a first date, because I respect the guts it takes to ask! So, when the lot eventually fell to me and he asked me on a date, I obliged. He picked me up in a minivan that desperately needed a car wash. He’d told me to dress for an “active” date, but our first stop was a greasy burger joint for burgers and shakes to eat on the way to our destination. We arrived at a trailhead just an hour or so before sunset. On our hike, he brought Ziplock baggies with “truth” questions and “dares,” which we would pull from depending on what number we rolled on a pair of dice (side note, rolling dice on a hiking trail is quite difficult). One “dare” I received was to be blindfolded and let him lead me along the path with his voice. I started to wonder if I was about to be murdered in these woods. I politely declined. As the “truth” questions ventured into “too deep for a first date” territory (“What aspect of your childhood trauma would make our relationship challenging?”), I decided to turn the tables and ask him why he thought he wasn’t married yet … could it be that his first date tactics were a bit off? The drive home was a bit quiet. – Kate Wartak
Best: It was New Year’s Day 1990, and my pastor invited me to come to a watch-or-don’t-watch Rose Bowl Party she and her husband were hosting. Unbeknownst to me, they’d also invited Mary (after trying unsuccessfully to connect us for months). Mary rang the doorbell, and Nancy answered it saying, “He’s here.” Six weeks later on Mary’s couch doing the Sunday crossword, I put the paper down and said, “You know I’m going to marry you.” She responded, “I know.” I asked, does that mean we’re engaged?” She said, “I guess so.” No bent knee, no diamond, no succumbing to the bridal-industrial complex. As I write, this week marks 35 years. I guess it took. – Ken Jones
Worst: There’s an important mistake that every unenlightened young man needs to learn, the earlier the better. This mistake begins with a disagreement with his date. And, in his infinite wisdom, he will not attribute his girl’s opposing opinion to thoughtfulness or a fresh perspective on a situation. Instead, the man concludes that his disagreeing girl is experiencing the mood swings of her menstrual cycle. And then, he will ask, out loud, with sincere misplaced confidence, “Is it that time of the month?” The ensuing rage with which his girl will rightly chew up and spit out, and possibly dump, his sexist, unthinking self, teaches a lesson that won’t be learned in textbooks. The earlier a young man asks this question, the sooner he will realize to never, under any circumstance, ask it again. Don’t ask me how I know. – Bryan Jarrell
Best: My husband and I were friends for a year before we started dating, so by the time he asked me out we knew each other pretty well, including that one of our favorite dining experiences was to go to a tapas restaurant and load up on plates. So that’s what we did, heading to a place near my apartment in NYC that I’d been wanting to try. We of course had a great time and ate way too much (coining for the first time my husband’s favorite post-restaurant phrase, “That was a lot of food”), and thus began our relationship. The next week, I was walking past the restaurant on the way to work in my new-love honeymoon haze when I noticed the windows were all papered up. Closer inspection revealed that it had been shut down due to rat feces contamination. So, sadly, we never made it back to the site of our first romantic dinner together, but luckily, we both survived the night and are still going strong seventeen years, two kids, a dog, and a move to Australia later. – Stephanie Phillips
Best (…?): It was a few days before my second year of seminary started and a friend of mine, JV, was throwing a back-to-school party. Having volunteered to help buy supplies, I went over to her student housing apartment to head to the grocery store. Without a keycard or physical key to get in, JV would routinely leave her kitchen window unlocked so I could throw it open and climb in “Clarissa Explains it All” style. That’s what I did this time. What I didn’t know was that JV wasn’t there, only her new roommate Hannah, whom I had never met, was and JV had neglected to tell her 1) that I was on my way and 2) how I got into the apartment. I opened the window, climbed in, and saw a look of horror on Hannah’s face as she just witnessed me breaking and entering her apartment. And that’s how I met my wife. – Will Ryan
