Relationship status: Single
Typical date: I usually go to the movies. I like to go out dancing. Honestly, I am not one of those internet people; I prefer to meet people at parties. I'm old-fashioned and hopelessly romantic; I like to dote on others.
Go-to outfit: A lot of dark clothes, especially in New York. Never heels. I do this thing where each month I'll wear one style of clothing over and over until I get bored of it. I like having a uniform. Usually I wear clean makeup, but when I go out I'll wear lipstick. Sometimes if I'm going dancing, I'll go all out, with colors everywhere.
Valentine's day plans: I'm actually DJing on Valentine's day at the Silent Barn. I'll do an opening mix and just chill with people after.
30, director of sales
Relationship status: Single, mother of Matilda (15 months).
Typical date: My dates pre-baby used to be like real marathon dates. I feel like all of my first dates have always been really long, traveling-around-town situations. But in the last couple of years, it's been really difficult to meet someone organically. It's very online-focused right now, which is really intimidating for me.
Go-to outfit: I'm really self-conscious about what I wear. The last first date I went on, I wore an oversized fisherman's sweater, baggy jeans, and motorcycle boots, because it was a blind date and I didn't want him to be focused on the way that I looked.
Valentine's day plans: I am actually working, because it's right in the middle of fashion week. Then I'm going to go home and make sugar cookies with Matilda.
Relationship status: Married.
Typical date: Because we have a seventh-month old baby, we try to go on a date once a month. It's not as spontaneous as it used to be. It's very planned and very meticulous, but at least it gives us that one night to feel special and remember that both of us are still a couple and that we do love each other. Our favorite restaurants are Barboncino in Prospect Heights, Bacchus on Atlantic Avenue, and Sweet Chick in Williamsburg.
Go-to outfit: My date looks are comfort that's still super glam. One of my favorite looks right now is this sequined look that is basically just sweatpants and a sweatshirt. I like to throw on fur. Before, I would get very excited about bright colors and prints and those things. Now, I'm trying to be a little bit more mature and streamlined.
Tip for feeling sexy: Lately I find that scents are more arousing for me. I barely wear perfume anymore, but when I throw it on, it kind perks me up and makes me exude my femininity a little bit more.
26, art advisor/curator
Relationship status: Newly single and flirty.
Go-to outfit: Something comfortable, because confidence is the sexiest thing to me. I don't have anything to hide, so I'm always trying to be myself. Nothing too over the top. I'm also not trying to scare them off.
Tip for feeling sexy: Recently it's been a few, fresh, all-white looks—tight white jeans and like a chunky boot. I make sure that shit just came out of the dry cleaner. It makes me feel so good.
Preferred way to meet new people: Instagram, Tinder, and IRL through the art world. Instagram DM is the new Tinder—it's the next level lurk. My DM is hotter than my Tinder, for sure.
Relationship status: Newly single.
Typical date: I really want to go to the rotating restaurant in Times Square. I would go on a Monday night, have a meal and a couple of cocktails, and then go to Vogue Knights, this weird Chippendale bar where all the vogue battles happen. By the time you come out the club, it's five in the morning; Times Square is totally silent, and all you can hear is, like, the buzzing of the billboards. Then, you can go get McDonalds and sit on the floor and eat french fries.
Go-to outfit: I never wear heels, really, because I am tall enough—five foot ten. I always want to be comfortable and ready for whatever. In my new dating life, I am going to put a cute dress on but still do me. I like living a lifestyle where you never know what you're going to end up doing that day.
What are your plans for Valentine's day? To be honest, I haven't even thought about it. I went to this meditation class the other day and somebody was like, "I call it Singles Awareness Day." And I feel like it's kind of a nice one to enjoy being alone, you know. I'm all about having my own moment right now.
25, freelance writer
Status: In a relationship since August.
Typical date: We don't really go on dates. I think our favorite date is what we call a floor picnic, which is our ordering takeout and sitting on my living room floor. We both work long hours. For our first date, we talked about how much we both loved R. Kelly and ended up watching Trapped in the Closet, which was really fun. We just went on a date to Nighthawk, because we hadn't been out in so long.
Tip for feeling sexy: For me, it's less about what I'm wearing on the outside and more about bras and stuff. I really like wearing button-down shirts to work and unbuttoning a button and going out at night. I don't like changing a lot. I like things that are transitional.
Valentine's day: Unfortunately, Fashion Week.
Relationship status: In a relationship for over three years.
Typical date: We're a pretty chill couple. We do a lot drinking together and hit lots of happy hours—not even the classiest ones. We love Turkey's Nest in Williamsburg. RIP Styrofoam to-go cups.
Go-to outfit: I always wear Vans, tight leggings, and a vintage band T. My boyfriend and I initially bonded over clothes; I was always into wearing boy's clothing and street wear. Still, I feel naked and grossed-out if I'm not wearing red lipstick and hoop earrings.
Valentine's day plans: I don't know what we are doing. I've hinted that I want to go back to White Castle. We did that on our first date.
27, freelance jack-of-all-trades
Relationship status: Single.
Typical date: I don't have a routine; it's more fun to switch it up. We are going to get to know each other, and at the same time, I am going to get to know this place; if one of them goes south, at least the other has a chance. The best date I ever went on I was when I was living in Tel Aviv, back when I used to date boys. This boy showed up at my apartment. He had two bottles of champagne, and was like, "Hey, let's go," and we just walked for hours.
Go-to outfit: My style is totally towards the androgynous side, so I veer into that dapper look, without trying to be cheesy. I definitely feel better in pants and something that's slick, as opposed to something feminine. Also, I wear Hermès every day. The cologne—it makes me feel great.
Valentine's day plans: My home girl and I are making dinner, and then we are going to see 50 Shades of Grey, and then we are going to China Chalet. Two years ago, we randomly found ourselves getting drinks on Valentine's day, because neither of us had anything to do. And this year we are both single again, so it's like, "Let's continue the tradition."
25, menswear publicist
Relationship status: Single.
Typical date: If I go out in my neighborhood, it's usually to a super-cute bar called Saint Maizie. They have jazz performers sometimes, and it's dimly lit and quiet. It's pretty sexy but, like, classy sexy.
Go-to outfit: Just jeans and sweater, since dates are usually right after work. But if we plan ahead of time, then I'll try to look put-together. I hate really high heels with a passion, and I only wear them if I have a work event.
Valentine's day plans: Nothing. I think House of Cards is coming out. I just binge-watched it last year and I will probably do that again this year.
Relationship status: Feyoncéd—we've been together for four years.
Typical date: When we have a super official date, we try to go to a gallery, a new restaurant, or a show, or we treat each other to a couple hours at Aire Ancient Baths. But on low-key date nights, Lil' Frankie's is our spot. Or maybe the Nitehawk movie theater, or Suzume in our hood. We once had an amazing breakfast date at Dimes.
Go-to outfit: Sexy tomboy? I almost never have time to go home before a date, so comfort ends up being part of the equation. The goal is to be the sexiest version of yourself, so you're not fidgeting or feeling like you're putting on someone else's personality.
Tip for feeling sexy: It's usually little things that make me more aware of my body and how I move. Like getting my nails done, or wearing stacks of delicate rings, or heels, or lipstick, or faux-fur.