Photo-Illustration: Marylu Herrera
In this week’s story, a wedding-dress stylist starts dating and having sex again: 23, single, New York.
DAY ONE
6 a.m. I’ve been trying to wrap my head around waking up alone and in a new apartment. This is all new to me. I recently broke off my engagement of three years. He was older, so he proposed after six months of dating. And I’m southern, so 20 didn’t feel crazy young to me to be engaged. I was excited to be a wife, but our love ran out. We were fighting a lot by the end, and I had a gut feeling that this wasn’t my destiny, so I ended it. I just moved into a new apartment a few weeks ago. It was hard, but I’m trying to stay positive.
I decide to go back to sleep since I don’t have to wake up for work today — I took a few days off to process everything from the past couple of months before I end up trauma-dumping on a random client. I work for a big events company as a wedding-dress stylist. The irony, I know.
12:45 p.m. Wake up again. It feels like it’s my job to get my head together before going back to work, so I try to just think about life for a while. I make some matcha and scroll Instagram and Netflix, but mostly I do nothing all day.
3 p.m. I really regret telling my friends I would go to a Fashion Week event tonight. However, I need to get out of my house and do something, anything.
7 p.m. Take a shower and start my getting-ready process. I’ve been bed-rotting all day, and the event starts at 9.
9:20 p.m. Fashionably late, I arrive. I grab a quick drink at the bar and join my friends. They hype me up and tell me that this is all for the best. They tell me to “go be single and 23.” I can’t remember the last time I was out with my friends without having to explain myself to my fiancé or feel guilty about what time I was headed home.
10:30 p.m. At the event, a Handsome Man approaches me. My friend shoots me a quick look and walks away. He is extremely tall, dark, and handsome and has the deepest brown eyes I have ever seen. He compliments my outfit and then my smile that follows. We end up hitting it off, grabbing our drinks, and meeting each other’s friends.
11 p.m. We’re alone in this corner of the party now. He kisses me and I get all the feels. Our friends interrupt here and there, and eventually we get pulled away to hang out with the groups we came with.
1 a.m. I get in a cab and head home. Handsome Man and I talk about meeting for dinner tomorrow. I wonder if he’ll follow through.
DAY TWO
11 a.m. I’m extremely hungover from all of the cheap Champagne I drank last night. I check my phone and find a text from Handsome Man: “See you tonight. Dinner at 6?” I freeze, realizing I don’t even know his last name, let alone what I said last night. I call the girls. I guess we really did have a lot of lose yourself make-out sessions. I respond to HM, “Sounds perfect.”
3 p.m. Shower. I have absolutely no clue what direction this date will take me. It’s my first date in ages, definitely my first date since breaking off my engagement. I feel this awful pit in my stomach that I’m doing something I shouldn’t be doing. But then I remember how undeniably hot this man is, and how when he kissed me, I could feel it all over my body, and then I feel better.
6:25 p.m. Arrive at the date spot and find HM sitting in the back at a dimly lit table for two. It’s with sober eyes that I realize he has to be at least 30, maybe even mid-30s, and damn, he’s hot.
8 p.m. We take a walk around the neighborhood after dinner. We talk politics and life. I’m starting to feel more comfortable around him, and even more attracted to him.
9:30 p.m. I’m in his apartment. I reluctantly agreed to come see “the view” — this has to be a tagline that New York men use as a ploy for sex. As I act completely blown away by this view of the East Village, I feel his arms wrapping around me and kissing my neck. He turns me around and picks me up, leading me to the bed. I blurt out, “I can’t have sex with you on the first date.” He pauses for a moment, then looks at me and says, “Trust me, baby, I get off by pleasuring women; we’re not doing that tonight.”
Midnight A couple of orgasms later, HM calls me a cab and walks me downstairs … no sex, no dick … just one very happy girl.
DAY THREE
10 a.m. I take a look around my apartment. Although I am extremely overjoyed by what happened last night, I’m reminded that this place is a wreck. There are boxes everywhere.
Noon With coffee in hand, I get to work on cleaning up this hot mess.
3 p.m. My phone starts buzzing and I pick up: It’s a call from the most fabulous person in my life, not only my best friend but my co-worker. He’s asking me if I’m coming to his going-away party tonight — shit, I completely forgot! It’s a normal workweek for everyone else who isn’t taking a week off to process a broken engagement and, most important, it’s his last day at our company. Of course I’m going. I immediately hang up and hop in the shower — I’m disgusting from moving boxes and cleaning.
6 p.m. Arrive at our regular bar to celebrate my best friend. As soon as I walk in, I can hear him shouting that I have a glow. Nobody knows what I did last night. A couple of drinks later, I’m sharing all the details of last night’s endeavor. I’m normally a pretty private person, but maybe I’m in my Samantha era.
10 p.m. We’re all having a great time as we normally do. I have a lot of friends at this company and I love when we’re all together. However, I’m begging to leave this bar … There are never any cute men here, and after last night I am feeling a huge wave of confidence. I have never felt more sexy in my life, and I intend to do something about it tonight.
1 a.m. New location, a gay bar … still no male prospects for me here. I find myself zoning out of conversations to drunkenly text Handsome Man: “Are you free tonight?” We haven’t talked since our date, so this is especially bold of me.
3 a.m. Cab home, no response from HM tonight.
DAY FOUR
11 a.m. Put in my AirPods for a walk around the park. I’ve been drinking way too much. I need to do a wholesome activity today. HM texts while I’m on my walk. It says, “Did you really booty call me last night lol.” I ignore for now.
1 p.m. Shower and relax. I think enough time has passed to text HM back. We make plans to see each other tonight, no dinner, just a casual hangout.
2 p.m. Get bored and make a Hinge account. I need more than one man on my roster so I don’t booty call just HM anymore. I start scrolling through all of the single men that Manhattan has to offer, putting my location where I assume hot men might live. I’ve decided now that I don’t really have a type, just someone who’s visually appealing and obsessed with me.
5 p.m. I’ve officially set myself up for success here: I have three dates this week. I’m giving myself something to look forward to; if nothing else, it’ll be a free drink at a new bar.
7 p.m. Call a cab to see HM. I feel less nervous tonight, but I do remind myself that if the sex is bad, I never have to see him again. In the car, I call some of my friends who don’t live in NYC and fill them in on my life. One long phone call later — about my crazy breakup, crazy orgasms with Handsome Man, and my three Hinge dates — my taxi driver informs me we’ve arrived. I pop in a piece of gum and walk up to the doorman.
9 p.m. Handsome Man has a great dick. We fuck on the bed, the wall, the couch, the floor. Needless to say, I will be seeing him again.
10 p.m. On my way out, I sheepishly look at the doorman, wondering if there are a lot of women that HM brings home. I walk out to the Uber and head home. I go back to work tomorrow, and oh my gosh, I cannot wait to tell my friends about tonight.
DAY FIVE
6 a.m. Wake up for work. Unfortunately, this morning, I find myself even more confused about my life than before. I just had the best sex ever and I feel on top of the world, but it feels like a lot of change all at once.
7 a.m. I turn on some happy music and go about my morning. Time to get on the subway.
12:45 p.m. Two clients down, two more to go. It’s weird for me to try to relate to the brides now — I used to feel like one of them.
3 p.m. I’m thinking about my Hinge date with a DJ tonight and what I’m going to wear.
7:30 p.m. I’ve decided on a bodysuit and jeans — literally nothing can go wrong there. I get on the subway to go meet this guy. I definitely feel nervous for this one. I’ve never met somebody on a dating app before, and this one is unusually attractive.
8:30 p.m. A couple of espresso martinis later and … okay, the DJ is hot as fuck. He’s also super down-to-earth, not a catfish, and he thinks I’m hot. I can tell by the way he pulled me in to kiss me. He says, “I’ve never met someone who can kiss like that.” I’m hooked. We agree to go to a quieter location for another drink.
10:30 p.m. We get another set of espresso martinis and sit in a back booth away from the crowd. He pulls me in closer, then uses that magic phrase: “Want to come see the view of the city from my rooftop,” I’m not even kidding — and with that we leave.
11 p.m. The view is amazing. It feels like a private rooftop. We’re making out, and all of a sudden I think I should have sex with him.
Midnight Let’s just say, the DJ can definitely make me sing. He walks me to my cab and we agree that we’ll be seeing each other soon.
DAY SIX
7 a.m. Wake up for work slightly hungover but buzzing from last night. I’m starting to feel more confident.
3 p.m. I walk down the halls of my company thinking about what dress to pull for my current client. We have a fashion closet that I dip into sometimes. Tonight, I’m meeting a doctor. Probably very classy. Maybe I could pull an Audrey Hepburn look of my own.
5:15 p.m. Head home to get ready for my date. He’s taking me to a nice bar that is shockingly near my apartment. I’m sure this is because he’s considerate. After all, he is a nice older doctor. He helps people for a living.
7 p.m. Thank goodness I wore a dress. It is unbelievably nice here! I get my signature gin cocktail while I wait. I can spot him entering the bar from a mile away. He is definitely over six feet tall, and I’m only five-three. He gives me a hug, and I feel like I’m hugging a teddy bear. His voice is assertive yet calming, and it makes me feel weirdly safe. We hit it off. He is very serious, definitely an introverted type A, so we depend on me — an extroverted type B — to take us through conversations.
8 p.m. I decide that after a few drinks, I want to go see my friends instead of cosplaying the doctor’s wife. He is pretty incredible in his own way, but I know it’s going to take me a couple dates to crack this egg.
9 p.m. I end up staying in and just texting a bunch of friends to fill them in on the doctor date.
DAY SEVEN
7 a.m. I get ready for work feeling light. I think I have finally wrapped my head around not being the engaged girl at work, and now, instead, getting to share my adventures with my co-workers and help them with relationship problems, too.
10 a.m. Starbucks run!
2 p.m. I think about all the beautiful brides I’ve been able to help this week, and it gives me hope for when I find the sexiest, funniest, kindest man of my dreams. I just pray I have a badass stylist who’s going through a self-awakening to help me find the perfect dress.
6:45 p.m. Wrapping up with my final client for the day. I am definitely late for my date tonight — he’s a consultant. I regret setting up three date nights in a row. I am exhausted.
7 p.m. I text the consultant asking for a rain check, and he agrees that it was a long day for us both. Instead, I’m going to endlessly scroll through Hinge for the evening. We agree to go out for coffee next week.
9 p.m. I end up meeting my girls at a local bar for a late drink. We’re all off tomorrow, so it’s a fun way to end the night. Across the bar, I see a man sitting alone watching the Yankees game. I ask our bartender if he’s with someone and he says “no.” I walk over. He greets me with a charming smile and the flirting starts up.
10 p.m. After a fun kiss good-bye, we agree to a date next week.
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