17 Women in Relationships Spill: What Did You Wear on Your First Date?

17 Women in Relationships Spill: What Did You Wear on Your First Date?
(Photo Illustration by Tanya Leigh Washington)

There are only a handful of times in life when you can recall, without fail, exactly what you were wearing—prom, your wedding, and, of course, your first date with that special someone.

We caught up with 17 women across America—all of whom are either married or in serious relationships—and asked them to tell us what they wore on their first dates with their now-significant-others. The responses ranged from surprising (a Juicy Couture jumpsuit!) to adorable (a polka-dotted Madewell dress) and everything in between.

Warning: Endless awwww's ahead.

Jordan, 28

Relationship status: Engaged
First date: January 2007
Activity: Saw Michael Clayton at the movies

Our mutual friend bailed on us for the movie, and I only started thinking it might be a date because he offered to pay. Then, he actually put his arm around me when I'd been shivering during the movie for about an hour. Here's the embarrassing part—I was wearing a black Juicy Couture sweatsuit! Juicy sweatsuits have no place on a first date—or anywhere anymore, for that matter. Guess that's what happens when you start out as friends!

Deena, 26
Relationship status: Dating
First date: October 15, 2008
Activity: Drank beer and played pool at a ("horrible, horrible") dive bar, then carved pumpkins at his house.

I kind of hated his guts at first, so the first date outfit was carefully calculated. He had been renting a room from my best friend, and I ran out of excuses—and things to do at the gym—to avoid him. Finally, he enticed me with pumpkin carving and somehow convinced me to go to the bar first. I didn't want to look like I tried at all, but I still wanted to look attractive just in case, so I just wore my pair of best-fitting jeans and a casual top with flat boots. For pumpkin carving, I brought black workout pants and a grubby T-shirt from the Santa Cruz Fungus Federation, so we at least had something funny to talk about while it was just the two of us. Surprisingly, he still talks about the gross pumpkin-carving outfit!

Casey, 28
Relationship status: Engaged
First date: December 2005
Activity: Dinner at a fancy Asian-fusion restaurant

It was all about the shoes on our first date, because I was concerned that my new suitor was too short. So when it came time to pick an outfit, I knew it had to go with low heels. I wore a lacy tank top, jeans, and black satin slingback Ann Taylor pumps.  I'd never worn them before because of the awkward height, but they became my go-to shoes in those first few months. It turns out my fiancé is taller than I gave him credit for and, to this day, I've never found a pair of shoes that make me taller than him!

Lenni, 22
Relationship status: Engaged
First date: October 1, 2010
Activity: Dinner at a Mexican steakhouse

We met at a college party when I filled his beer cup at the keg. "Oh, you don't have to pour my beer for me, that's alright," he said. We ended up ignoring everyone else the whole night, and he asked if he could take me out for dinner the next weekend. I wanted to look cute while feeling completely comfortable, so I wore a lightweight strapless Charlotte Russe dress with Michael Kors wedges and a Forever 21 crossbody bag. I wanted everything to go perfectly—and by "perfectly" I meant we'd maintain a great conversation, and I'd make it through the night without tripping in my heels. Now we're engaged, and I will forever be his beer girl!

Jamie, 35
Relationship status: Married
First date: August 2001
Activity: A play (on roller skates!) then dinner at Katz's Deli in New York

We were set up on a surprise blind date and ended up at a very bad fringe fest play—on roller skates! It was in the Lower East Side, back when it was just dirty and not cool. I wore a red-and-navy-blue striped short-sleeve shirt (it was tight!) and black jazz pants because I had just come from ballet class. I finished the look off with black flip-flops. I remember our conversation on the street involved the phrase "hot garbage." How could I resist?

Liz, 24
Relationship status: Engaged
First date: August 2010
Activity: Dinner at a Japanese steakhouse followed by a trip to The Big Tree

We were going through law school orientation together, so our first official date was really a night out after turning in some homework. We went to dinner and then drove out to this huge tree in the middle of nowhere. It's a cool thing to do at night because you can see the stars. I wore a sleeveless black cotton dress from Target that had ruffles along the neckline and black J.Crew sandals. Heels were way too dressy before nightfall in our college town. If I had our first date now, I would pick something a little more fun. But I knew he thought his ex wore some ugly dresses—they were too trendy—so I wanted a more classic look. Clearly it worked, though—we're now engaged, two years later!

Lindsay, 23
Relationship status: Dating
First date: February 22, 2012
Activity: Went to a hole-in-the wall piano bar then grabbed dinner afterwards

We met on OKCupid and talked on the phone for hours before we finally met. He suggested a bar/restaurant in New York. I wore a black-and-white polka-dotted Madewell dress that hit at mid-thigh and had sheer ruched sleeves that came down to my elbows. I paired it with black tights and black over-the-knee boots. I didn't want to be over-the-top for a first date but I very much wanted to look like myself. The outfit was flirty but not crazy!

Jordan, 25
Relationship status: Married
First date: October 2009
Activity: Lunch

I misplaced my phone at a bar, and I turned to a random guy next to me and asked if he'd call it. That's how he got my number—and he called every morning for two weeks trying to get me to go on a date with him. I finally agreed to lunch. It wasn't a well-planned adventure, so I just had regular work clothes on for the first date—Khaki Dockers capri pants and a white long-sleeved button-down with brown strappy wedges. He came by my office to pick me up and all the ladies were standing at the window trying to catch a glimpse. I made him get out and wave so they could!

Anna, 23
Relationship status: Dating
First date: April 24, 2012
Activity: Dinner at a Thai restaurant and dessert at a chocolate shop

We worked together for six months before he asked me out. We met up for drinks, and the rest is history! I remember stressing about what to wear because he'd seen me in so many outfits at work, so I thought maybe I should wear something new and fresh—like, this is Date-Anna, not Work-Anna. I was so nervous, my roommates suggested I wear something I felt comfortable in. I ended up wearing a black top that I love because it fits me like a glove, with a green, silver, and black print skirt. It was an outfit I had worn around him several times before, but it still made me feel sexy!

Ally, 25
Relationship status: Engaged
First date: June 6, 2010
Activity: A St. Louis Cardinals baseball game then dinner afterwards

We'd been hanging out for a while just as friends, but we were both secretly interested in more than that. Technically our first date was a St. Louis Cardinals baseball game, but we didn't even call it until after the fact when we were sitting at dinner and both agreed that it was an "official" first date. So my first-date outfit with Garrett ending up being a Cardinals shirt from Victoria's Secret and boyfriend-fit jean shorts.

Olivia, 29
Relationship status: Married
First date: 1999
Activity: Group date movie

I don’t really remember my first date outfit, but lucky for me he did! Apparently, I was wearing a Hurley shirt and jeans—I was 16 at the time!—which sounds super-stylish, right?

Brooke, 24
Relationship status: Dating
First date: May 2011
Activity: A Super Mario competition followed by sushi

We were friends beforehand, so grabbing sushi was a mutual decision—and then I invited him over for the video games! Sadly, I have no idea what I wore on our first date, but I'm positive it was something casual. Skinny jeans, a basic tank, and flip flops sound about right. It's funny, though, because I can remember what he wore—a black V-neck, grey shorts, and black vans. Complete with a flatbill hat.

Victoria, 27
Relationship status: Engaged
First date: February 2009
Activity: Dinner

My guy (who was on my brother's hockey team at the time) was returning from a trip and asked if I wanted to do something when he got back into town. Naturally, I said yes! We decided to go out for dinner. After trying on everything in my wardrobe, I decided on a lace peplum top and black skinny jeans with heels. Classy but sassy, I thought, and appropriate attire for almost any local restaurant. By the way, I just asked him if he remembers what I wore on our first date, and he's convinced I wore a Little Black Dress. A little wishful thinking, perhaps?

Jill, 30
Relationship status: Married
First date: May 2001
Activity: Went to a Chicago Cubs baseball game

We were in a gen-ed class together in college, and he asked me if I wanted to hang out with him and his friends at a baseball game in the city. I wore a really casual outfit—jeans and a sweatshirt—because I didn't think it was a date, and I didn't want to be cold. But when we got to the game I noticed that all of his "friends" were actually his fraternity brothers and that they all had dates. I asked him if this game was actually a frat date party, and he sheepishly admitted that it was, but said that he didn't want to scare me off by asking me on an official date. So basically I got tricked into our first date, and I was woefully under-dressed for it. It ended up working out well enough, though!

Crea, 24
Relationship status: Dating
First date: March 2008
Activity: Saw the movie Taken

He called after a drunken night out at the bar and asked me to a movie. There isn't much to do in Athens, Ohio outside of that or dinner at a bar, so I chose the movie! I wore a cream top with lace detailing, a blazer, dark skinny jeans, and red kitten heels. It was simple and casual, yet looked put-together. I thought the outfit was movie-casual but he thought differently—he commented that I was “so dressed-up!” Most people at the Ohio University movie theater on a Sunday were in sweatpants and hoodies, so maybe it was a little bit dressy for the setting.

Alicia, 27
Relationship status: Engaged
First date: June 2006
Activity: A concert followed up by a day at the beach

It's kind of hard to say when my fiancé and I had our first date—we'd been friends for years and, as we learned later, had crushed on each other for almost as long. We went to a concert together in early June, and I hadn't yet learned that even the balmiest San Francisco evenings come with a gloomy dose of fog. So I slipped into a short striped dress from H&M and a pair of pointy-toed silver heels—they were the only pair I could dance in! I didn't choose quite so wisely when Tony and I took our first weekend outing together a few days later: Pink glitter kitten heels aren't really good for beach hikes. The rest of the ensemble was quintessential me in 2006: All color, all silly, with glittery rhinestone strawberry earrings to complement my stupid pirate shirt. I miss my old Replay racer jacket!

Lauren, 24
Relationship status: Dating
First date: April 19, 2010
Activity: Had drinks at Cask in New York

We met at a bar, and when we exchanged numbers, I gave him mine and said, "Don't call me." The next morning, I texted him and asked to hang out! We ended up grabbing drinks at a bar—I pretended to actually enjoy beer and consequently was stuck sucking down 650 ML of cider. I wore a blue-and-white striped boat neck shirt, skinny jeans, two-toned beige J.Crew flats, and a tan trench coat. I also had my roommate curl my hair, which definitely set unrealistic expectations about my hair routine!

So, what do you think? Which was your favorite first-date outfit and first date story? Share your story with us in the comments below!

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