This week, a woman new to New York considers her sugar-daddy options: Female, 21, single, straight, Washington Heights.
DAY ONE
10:12 a.m. I wake up to my phone ringing. It’s my mom. I quickly hit ignore so the sound doesn’t wake my three roommates. Since I moved to New York just a few weeks ago, my mom’s been extra anxious about staying in contact. Every night she texts and asks if I’m back in my apartment yet. Last night I lied, responding to her good-night text from the bar at the Edition, where I was have a cocktail with J, a potential new sugar daddy. Now I’m hungover and not ready to think about the date I ended up fleeing, so I go back to sleep.
10:49 a.m. When I wake up again I have a text from C, my sugar daddy from college.
Last night around 11 p.m. I drunk-texted C while I was hiding from my date in a CVS. Now I’m embarrassed. C was my first-ever sugar daddy (I’ve met them all on Seeking Arrangements), and I was always proud of myself for not developing feelings for him. But since moving to New York, I’ve found I’ve been reaching out to him more and more. The frustrating search for a new sugar daddy has made me realize how lucky I was to have C. I fill him in on the details of last night’s disastrous date with J.
I could tell early on that J was kind of a dick — but that’s also to be expected, to a certain degree. Still, when he wanted to take me home I told him I’d be more comfortable getting a room at the hotel, and he tried to fight me on it but eventually agreed. Then when he went to book the room he got so aggressive with the staff that they literally threatened to kick him out. So I just turned and ran out of there and sprinted three blocks away.
Once I send the text I start to wonder if I overreacted. Maybe I should have stuck it out for the $600 J was offering. I ask C for his expert opinion. Was the hotel room an unreasonable request? C says that I should only go back to a stranger’s apartment if I don’t care about my safety.
12:05 p.m. I head to a nearby café to do some work on an edit test for a job I’m applying for. I just graduated from college and moved to New York for an editorial internship. It’s my dream magazine internship, but I landed it just a little too late. Student loans are going to kick in soon. I need a real job. And a sugar daddy.
I first joined the SA app as a freshman in college (I had read about it online), but I didn’t actually meet anyone from it and start really sugar dating until my senior year of college. It definitely made me more nervous than other dating apps, which is why it took me so long to go through with it. But when I started my last semester of college, I knew I would want to move to New York after graduation and would need money. It finally felt like the right time for me to try sugar dating for real.
Once I got my first sugar daddy, C, I actually regretted not doing it sooner. To my surprise, I didn’t have any feeling of weirdness or shame. A joke I sometimes make is that if anything, I find it much more demeaning that I was having sex with men for free for four years before this. My first experience sugaring was much more fun and fulfilling than I expected, and in some ways I actually found it more fulfilling than traditional romantic relationships. My close friends know about it and have always been accepting/supportive, although I’m the only person in my friend group doing it. My family doesn’t know.
12:17 p.m. I open up my laptop to find more texts from J from last night. I guess some came through on my computer even after I blocked him.
J: You just took off?
J: What a bitch.
J: Fuck you.
J: CUNT!
2:30 p.m. I make plans to meet up with another guy from Seeking Arrangement on Wednesday after work. JP is young, only 36, which makes me nervous. I don’t trust the ones under 40. They usually try to just use the app like Tinder. But JP agrees to $600 per meet, which seems to be the going rate.
9:23 p.m. I go back to my apartment. It’s a four-bedroom in Washington Heights with two to six girls per room. Is this even legal? I’m not sure.
Scrolling through SA, I think about what C said about the guy from last night: He was single? Red flag. As awful as it sounds, he’s right. At least you know the married ones are sane enough to convince someone to marry them. C is married with two teenage daughters. I was always surprised by how little it bothered me.
DAY TWO
7 a.m. I plan to text Ray today. Ray is the guy I fell in love with last summer, when I first moved to the city for an internship between my junior and senior years. He was a tall, handsome, 37-year-old marketing director on the Upper West Side. I spent almost every weekend that summer between his bed and his private rooftop. I haven’t seen him since my last night in the city in August, when I got high, told him I loved him, then cried myself to sleep in his bed. He’s kept in touch from time to time. He has connections in the industry, so last week I finally got up the courage to ask him for a referral for a job I’m applying to. I’m applying for another one now, and I’m going to reach out for his help again. I’ve been waiting to text him since Friday.
1:33 p.m. When I texted Ray about the last job, I kept waiting for him to ask me to hang out. When I confessed my feelings at the end of the summer, I knew he didn’t see a future for us, but I couldn’t help but hope that would change when I moved back to the city.
3:50 p.m. The Poet texts. He wants to get drinks on Thursday. We had our first date last week. I know I need to focus on sugaring and don’t have time for real dates, but it’s nice to have a crush again. He’s the first real person I’ve dated since Ray. They’re about the same age, late 30s, dark hair, UWS dwellers.
7 p.m. I’m on my way to look at an apartment in Astoria. It’s one of the coldest days yet this winter, but the 13-minute walk from the subway stop to the new apartment is definitely worth the promise of escaping my current living situation. I’d be sharing my new apartment with three other strangers instead of 14. This apartment seems fine, and I can move in at the end of the month, but for now it’s back to my bunk bed in Washington Heights.
10:45 p.m. Ready for bed, and thinking I’ll wait to text Ray till tomorrow.
DAY THREE
9:40 a.m. I finally text Ray about the job while I’m at the gym. As soon as I send the message I feel like I’m going to throw up.
10 a.m. I get to my internship. It’s full-time, M-F, 10-6. It’s a print internship, but I would prefer digital. The pace of print has been even slower than I expected. It’s primarily a fact-checking position, but I want to be writing.
12:31 p.m. Ray texts back and says they’re looking for someone with a few more years of post-college experience. This industry is for rich kids who have more time and less debt. I’m starting to regret using Ray as a professional contact anyway. Every time he texts I’m just disappointed it’s not to ask me out. And I don’t love that I’ve given him a front-row seat to my professional failure.
11:35 p.m. Back home, showered and in bed, I finally read another text from Ray. He says he’s happy to keep helping and I can feel free to “abuse his generosity” (he’s borrowing my words) as much I like.
DAY FOUR
7:47 a.m. B texts, finally. B and I matched on Tinder about a month ago, but we still haven’t met. I somehow talked him into sugaring, and he was surprisingly into it. He’s 43. He calls me Kitten, which is repulsive and yet somehow I’m kind of into it. He Venmo’d me $500, and teased me with promises of Louboutins and La Perla. His intensity was equal parts sexy and scary. I almost canceled our first date, until he ghosted on me instead. I was surprised by how disappointed I was. Now he’s back, and so is the intensity. I tell him about my night with J and show him the screenshots.
B: He’s definitely not allowed to call Daddy’s little angel the C word.
10 a.m. I’m at my internship all day again. It’s only my second week, and work is still slow. I mostly work with one other intern, a 22-year-old guy. We’re friendly but don’t talk much. Mostly he just reminds me that I’ve never really known how to interact with men my own age.
10:24 a.m. I ask B when I get to see him. He says: Tomorrow. SIXTY Soho.
Tomorrow I’m getting drinks with the Poet. I know I shouldn’t waste my time on real dates, but I can’t bring myself to cancel. I lie and say I have a work event and ask if we can do Friday instead. B: No. Tonight then. Me: Okay, tonight. B: If there’s any reason to feel uncomfortable, tell me. And I’m sorry on behalf of my gender that you had that happen this weekend.
11:39 a.m. Once B starts texting he doesn’t stop. B: I know that we will both get what we need tonight. B: Let me put it this way. B: I will be in you. B: Also. I don’t want you meeting sketchy guys. B: From now on, I want to be the only guy who comes in you.
I know I’m still going to sleep with the Poet anyway.
3 p.m. Haven’t heard from B in a bit and I’m starting to worry he’ll ghost again.
5:53 p.m. I shoot B a text to confirm before I leave work. By the time I get on the train I already know he’s not going to respond, but I check my phone at every stop anyway.
6:37 p.m. I send B three more texts.
6:48 p.m. I know he’s not going to reply, so I just get ready to go to the gym instead. On my way out, I call him. He doesn’t pick up, and he doesn’t even have an answering message recorded. For the first time, I consider the reality that I have no idea who this stranger is. In all my years of dating apps, this may be my first catfish.
7:28 p.m. I text him again.
Me: Hi. Can you just explain to me what the hell this weird game you’re playing is and what the fuck it does for you?
I haven’t lost it on a dude for ghosting like this since I was a teenager.
11:45 p.m. I get home, shower, and go to bed annoyed. I Venmo request B $500 “for wasting my evening.”
DAY FIVE
7 a.m. I’m having drinks with the Poet tonight. I could use a night off from sugaring.
7:12 a.m. B texts.
B: My sister has not been seen or heard from since January 4.
B: I spent my afternoon/evening/night calling police/hospitals.
I don’t know what to do with this or even if I believe it. I can’t ignore red flags. I don’t respond.
4:15 p.m. Work is still slow, there’s a lot of downtime. The office is already pretty empty, and one of the other magazines on our floor is moving out today, so it’s even more vacant. Hardly the lively, fast-paced environment I expected from the newsroom of a major magazine. Print is dying a slow death and sometimes I think it would be better if we just put it out of its misery.
7:30 p.m. I meet up with the Poet at an UWS bar. We talk about art and writing and the classes he’s teaching this semester. I bring up astrology and am pleasantly surprised that he takes it seriously.
9:15 p.m. Turns out the Poet has to meet friends for a late dinner. Sounds like an excuse, but I think I believe him. Still, I’m a little annoyed, so I offer only a few closed-mouthed kisses instead of last week’s mid-sidewalk make-out.
9:45 p.m. I get home just drunk enough to be tired and annoyed. I fall asleep with my makeup on and my contacts in.
DAY SIX
10 a.m. C sends me a picture of his new sugar baby, a tan blonde, and I’m annoyed. blonde. He’s always preferred blondes — he’s told me I’m one of only two dark-haired women he’s ever dated. Looking at the picture again, I’m annoyed that I’m annoyed.
10:37 a.m. My first paycheck came in today. I’m barely making $400 a week.
12:23 p.m. I make dinner plans with another SA guy I’ve been texting — M, in finance, 48. Scrolling back through our message thread on the app, I see he first messaged me seven months ago. Back then he was offering $700 per meet. I hope the offer still stands, but I don’t want to put him off by talking money too early.
3:17 p.m. News of media-industry layoffs keeps breaking. The reality that I am taking massive risks to enter an industry that regularly fucks over even established, talented professionals is getting harder to ignore.
8:30 p.m. I’m late to dinner and I can tell M is annoyed. The conversation isn’t flowing and we don’t have the same sense of humor. He tells me he found me off-putting online. This shouldn’t hurt my feelings, but it does.
8:45 p.m. I’m telling M about my experience running away from J, and he says that it was “absolutely ridiculous” for me to have insisted on getting a hotel room. I still have some lingering regrets about passing up the money I would’ve gotten from J and I don’t want to make the same mistake again, so when M asks if I’ll go back to his place, I decide to take the risk.
10:15 p.m. Back in his apartment, I ask him if he has any wine. “Nope,” he says, putting his hands on me. When it’s over, he finishes on my face. “That was fun,” he says, lying next to me on the bed. But I’m hit with a wave of emotion and start crying.
12:20 a.m. M is surprisingly understanding about the crying. I tell him about how scared I am, of the future I’m trying to build, of my student debt. He tells me about a previous sugar baby who made $250,000 a year from the site. He tells me I could do that too. He is brusque, but honest. I cry the whole time.
1:12 a.m. M gives me $700 in cash. Before I leave he asks if I want a hug. To my surprise, I do. He is still fully naked, but there is nothing sexual in his embrace. Hugging this stranger, crying, I realize I don’t remember the last time I was held.
DAY SEVEN
10:30 a.m. My face is still swollen from crying when I wake up. I have a non-sugar date tonight with a 44-year-old finance guy from Bumble.
11:34 a.m. I agree to get drinks with D from Riverdale before the Bumble date. He’s 54 but seems older. We met up once last week and I was immediately repulsed. But he’s offering $6,000 a month, so I’m reconsidering.
6:15 p.m. I get to the hotel bar where I’m meeting D. We sit down and he puts his hand on my thigh. He tells me about his cancer, and I wonder if I can somehow convert my revulsion for this man into sympathy. He tries to hold my hand and I would almost prefer he kept it on my leg. I recoil instinctively and he ends up grasping onto a few tense fingers.
7:45 p.m. Before I leave for my date, D hands me two $50 bills. In two days, I’ve made as much money as I make in two weeks at work. I tell D I’ll see him again, and I still don’t know if I’m lying. I just don’t know if I could go through with that, even though I know if I don’t take his $6,000 some other, smarter girl will.
8:00 p.m. Bumble guy is kind and funny. We get along well and have plenty to talk about. We stay out late and get very drunk. But I don’t kiss him good night, and I’m not sure why.
1:52 a.m. Back home and in bed, I want to text Ray. I want to text him and ask him if he’s sure whatever parts of me he could’ve loved aren’t enough. But I don’t.
Want to submit a sex diary? Email sexdiaries@nymag.com and tell us a little about yourself.
