Domestic Dramedy: Our First Valentine’s Day Date Night Was a Thrift Store Fashion Crime
Several years ago, back when Scott and I were dating long-distance, he lived in Ohio and I lived in Tennessee. That meant our relationship was built on phone calls, countdowns, airport pickups, road trips, and trying to cram three months’ worth of togetherness into one week.
I usually flew up to Ohio every few months because my job was a little more flexible. As long as I had an internet connection, I could work, and I had way more PTO than he did. But one February visit was different. I was going to be there for Valentine’s Day.
This wasn’t just any Valentine’s Day. It was our first Valentine’s Day in the same state, so naturally, we wanted to make it special. Also naturally, because this is my life and apparently nothing can just be normal, the whole trip started with a car wreck.
Since we were also celebrating a late Christmas, I had a bunch of gifts to take with me and knew I’d be coming back with gifts too. Flying wasn’t going to work unless I planned to wrap myself in presents and board the plane looking like a clearance-rack Santa. So I decided to drive.
My car at the time was already entering its senior citizen era. You know that stage where it technically still runs, but you talk sweet to it before every trip and pretend you don’t hear that new noise? I figured the smart adult thing to do was rent a car.
That turned out to be a mistake.
The night before I was supposed to leave, I ran to the store for road trip snacks. Because obviously no long-distance trip can begin without chips, chocolate, caffeine, and enough sodium to preserve a small ham.
On my way home...
BAM.
A minivan T-boned me. The rental car crumpled. My soul briefly left my body. Thankfully, nobody was hurt, and the car was still drivable.
To this day, that has been my one and only wreck. And because I am apparently the kind of woman who can get T-boned at night and still think, “Well, I need to leave on time tomorrow,” I handled it in true Serena fashion. I made a claim with the rental car company and with my insurance, then drove the wrecked rental car to the airport rental agency because it was the only location open at 10:00 p.m.
I basically walked in and said, “Hi. So funny story. I broke this one. Can I have another?”
They looked up the claim, then ran outside to inspect the car where I’d parked it. A minute later, they came back in laughing. I mean, I was fine, the other driver was fine, and the claim was filed, so apparently, we had reached the comedy portion of the evening.
They handed me keys to another car and gave me one simple instruction: “Try to bring this one back looking less like an accordion.”
Fair. A little hurtful. But fair.
The next morning, I left for Ohio like nothing had happened. Because apparently love waits for no bumper.
Thankfully, the rest of the drive was uneventful. When I got there, Scott had flowers, chocolate, and all the little things I loved waiting in the room. It was sweet and thoughtful, and I remember thinking, “This Valentine’s Day is going to be epic.”
I was not wrong.
I got there a couple of days early, and in true Scott fashion, he didn’t have some big, polished plan. His plan was basically, “You’re here. I’m here. Let’s spend time together.” And honestly, when you’re dating long-distance, that’s enough.
At some point, we started talking about what we wanted to do for Valentine’s Day. We didn’t want anything fancy. We didn’t need some big, expensive, candlelit production. We just wanted something fun and memorable. That’s when we hatched the thrift store date night idea.
We decided each of us would go into a thrift store, pick out an outfit for the other person, and then wear whatever the other one picked on our Valentine’s Day date. Later on, after we had already done it, we started seeing other couples on TikTok doing the same kind of thing. Naturally, we handled that with maturity. By which I mean we joked that they clearly stole our idea, because obviously Scott and I are pioneers of romance, questionable fashion, and public embarrassment on a budget.
So the day before Valentine’s Day, we started hitting thrift stores. The rules were simple:
We could only spend $25 each;
We had to check out separately so our picks stayed secret; and
The outfit had to be weather appropriate.
That last rule mattered because it was Ohio in February, and the temperature was somewhere between single digits and “why do humans live here?” As much as I would’ve loved to dress Scott in a spaghetti strap prom dress, it was just too cold. I’m not heartless. Questionable? Yes. Heartless? No.
We finally found a thrift store, exchanged sizes, and went our separate ways like two bargain-bin fashion villains. We spent at least an hour picking out each other’s outfits. And because we are us, we did not aim for cute. We aimed for unforgettable.
I found Scott a pair of blue-green corduroy pants that were about three inches too short, a black button-up shirt with large green polka dots, a mustard yellow vest, and a fake leather jacket that looked like it had once been rejected by Kmart. He was styling. Not well. But he was styling.
Scott, meanwhile, picked out my outfit with what I can only describe as enthusiasm and possibly revenge. He got me a red skirt with white dots, a pastel striped crinkly button-down shirt, a big fuzzy scarf, a white and black houndstooth blazer and a rainbow bedazzled headband. The outfit looked like a substitute teacher, a Valentine’s Day clearance rack, and a preschool craft project got into a fistfight.
The next day was the big reveal, and let me tell you, it did not disappoint. We laughed so hard we were crying. Nothing matched. Nothing fit quite right. Everything was just a little bit off, which honestly made it perfect.
Then, because apparently the clothes were not enough, we decided we also got to do each other’s hair. I gave Scott a slicked-down middle part, and he put my hair in pigtails. At that point, we looked less like a romantic couple and more like we had escaped from two different low-budget theater productions.
And then we went to dinner. Our destination? The Spaghetti Warehouse. Because nothing says romance like pasta, freezing weather, ugly thrift store outfits, and walking into a restaurant looking like you lost a bet with your own closet.
Everywhere we went, people stared, which, to be fair, was not an unreasonable response. Some people loved it. Some people looked at us like we were completely crazy. One couple stared so long that when Scott finally looked over at them, they jerked their heads forward like they had not just been visually auditing our entire life choices.
They clearly thought we needed a responsible adult, a clipboard, and possibly matching wristbands. Scott could not hold in his laughter.
The wait staff was especially fun. They laughed with us, took pictures, and started telling us about their own funny couple adventures. Suddenly, our ridiculous date had turned into a whole conversation starter. And we didn’t care who thought we were nuts. We were having the best night.
That’s what I remember most. Not the food. Not the weather, except for the part where I’m from the South and we don’t do negative 345 degrees. Not even the fact that Scott looked like a clearance-rack magician with cold ankles.
I remember laughing and feeling happy. I remember thinking, “This is exactly why I love him.”
That first Valentine’s Day together was not fancy, not expensive, and certainly not polished. It was a $25 thrift store challenge, ugly pants, a fuzzy scarf, pasta, confused strangers, and the kind of laughter that still makes me smile years later. And honestly, that was better than perfect.
And because this is Scott we are talking about, that outfit did not retire after Valentine’s Day. Several months later, I flew back up to Ohio for another visit. I got off the plane, started walking through the airport, and there he was.
The man. The legend. The thrift store nightmare.
He was standing there in the same outfit. The too-short blue-green corduroy pants. The black shirt with green polka dots. The mustard yellow vest. The fake leather jacket had been retired at that point because it was too hot to attempt that monstrosity again.
And yes, he had done his hair the exact same way. Slicked down with that middle part like he was reporting for duty at the Department of Questionable Fashion. People were staring, because of course they were.
And there I was, walking toward him, laughing so hard I could barely breathe while also loudly denying that I knew that crazy man.
“Who is that? I have no idea who that is.”
Meanwhile, I was walking straight to him. Because unfortunately for my reputation, that crazy man was mine. And I loved it.
When you’re in a long-distance relationship, you learn pretty fast that the little moments matter. The silly ideas matter. The willingness to show up matters. The ability to laugh together matters.
You don’t always need a fancy restaurant or some huge romantic plan. Sometimes love looks like driving several states after a rental car disaster because you just want to see your person. Sometimes love looks like flowers and chocolate waiting for you. Sometimes love looks like a man willingly wearing too-short corduroy pants in public because he knows it’ll make you laugh.
And sometimes, if you’re really lucky, love looks absolutely ridiculous.
I think we put a lot of pressure on special days to look a certain way. Valentine’s Day is supposed to be romantic, polished, and picture-perfect. But some of the best memories don’t come from perfect plans.
They come from joy and laughter. They come from the weird little moments you never could have planned but somehow never forget.
That Valentine’s Day reminded me that love doesn’t have to look perfect to be real. Sometimes God gives us joy right in the middle of the ridiculous. Sometimes He gives us memories wrapped in ugly corduroy pants and a mustard yellow vest.
And sometimes the blessing is not the perfect date. It’s the person standing beside you, fully committed to making you laugh, even if half the restaurant is staring.
“A joyful heart is good medicine, but a crushed spirit dries up the bones.” Proverbs 17:22
