The Kindergarten Teacher Ending a Yearlong Dry Spell

In this week’s story, a woman goes on a second date and gets rejected by a man she met on the subway: 41, single, Queens

DAY ONE

6 a.m. Wake up to Whisky demanding breakfast. My apartment is silent except for her little meows, which sound sick. I rub my eyes. The past few days have been an endless loop of anxiety — dating without any luck whatsoever, Whisky’s illness, school chaos. I’m a kindergarten teacher at a school in the city.

8 a.m. Sip my coffee in the classroom before the kids get here. My hands are trembling slightly. Sometimes I wonder if I’m heading toward a nervous breakdown from all the dating and centering of men who don’t care about me. Then I think, You’re gonna have a nervous breakdown because you can’t meet a guy? Get over it! I dunno. Lately, the weight of being single and looking for love is too much.

1 p.m. Quick break from work. Other teachers, many of whom I consider friends, talk about their kids and busy lives. My life is so small in comparison. One of the teachers, Rena, is so funny with how she talks about sex. (Of course, when no kids are around.) She’s a divorced horndog. As for me, I’ve never really craved sex. Intimacy, yes. Love, absolutely. Sex, I can take or leave. There’s always the possibility that I haven’t met the man to unlock my love of sex yet.

3:45 p.m. My phone buzzes. I get excited thinking that it’s Bushwick guy, a sexy artist I met on the apps. It’s not. It’s Spectrum. Bushwick and I went out to a wine bar last week. The date was great, but at the end, it took a hard left turn: Out of the blue, he asked me, “Do you like to fuck?” I froze and got weird, then pretty much ran away from the date.

I regretted it later. I didn’t have to be so uncool about it, and he intrigued me even if the question was … surprising. So I asked him for a do-over. That’s supposed to happen this week, but I’m still waiting for him to confirm.

6 p.m. I send a casual text to a guy I met last week on the subway. I was reading a review of that TV show Task on my phone, and he looked over and mentioned that he was a fan, too. It was very cute. Before he ran off the train, he asked for my Instagram. Within an hour, he DM’d about meeting up this week. We made vague plans for tonight or tomorrow, but it’s his turn to DM back …

9:20 p.m. Nothing from Bushwick. Nothing from Task. Argh. I often wonder if I should just give up on dating. Maybe I’m not cut out for it. It’s been about ten years since my last relationship. A decade of searching for a boyfriend. It’s sickening, when you think about it.

DAY TWO

6:45 a.m. Pack some leftovers for lunch, a simple pasta with homemade sauce. I’m Italian; my sauce itself should be enough to get me a husband.

8:10 a.m. Just before the kids arrive, Task writes that he’s just getting serious with someone and doesn’t think a “meetup” is a good idea. Jesus Christ, it was his idea! Delete and block. Every rejection, every ghost … it chips away at my soul.

12:15 p.m. No reply from Bushwick. Our date do-over was supposed to be tomorrow. Maybe I should get plastic surgery. Maybe hire a stylist? Maybe I should start drinking more or taking pills or acting more crazy and fun? This is what occupies real estate in my head when I’m not teaching 5-year-olds not to pick their noses.

5 p.m. Drinks with Lara, my best friend since childhood. She’s always busy with her three kids, but she knows I’m too fragile to bail on these days. I vent about the ghosting and feeling like I’m running out of time. She always tells me the same thing, that men are simple: They want a fun girl who likes to fuck. It’s funny, and I think it’s kind of true. We decide I’m going to dial up my sexuality, and that, on my next date, I’m going to embody someone more like Rena from work — a funny, sexy good time. I ask Lara how I’m supposed to do that and we both agree: alcohol.

8 p.m. Bushwick writes and apologizes for his lapse in responding, saying he’s been “slammed.” Yeah, slamming women, I think — because my impression is, he’s basically unemployed? Short story short: We’re on for tomorrow! Considering this is a man who blatantly asked me if I’m down to fuck, this probably means sex. I’m ready for it!

DAY THREE

6 a.m. Whisky wakes me up. She’s really old, has all kinds of issues, and there’s nothing more I can really do for her at this point. I switch to thinking about my date tonight. Should I call in sick to work? It’s so tempting, but I decide against it.

10 a.m. My head is filled with worries. The plan is to run home after school and then meet Bushwick in … Bushwick. I have a car, so that’s no problem, but then again, I want to drink, so that I can fuck, so that means no driving. Okay. Of course, that’s only if I want to fuck. Ugh! I’m so anxious thinking about all of this, and have to refocus and get back to reading lessons. I’m already losing my mind, I don’t need to lose my job too.

2:45 p.m. I leave school the second I can. There’s a Zara nearby. I buy a bunch of tops — most of them are black and sheer — to try on at home. I’ll return whatever I don’t wear later this week.

5:40 p.m. After a long shower, I’m smooth everywhere and I smell like nectarines and honey. As I get dressed, it’s like I’m putting on a costume. That’s the theme of tonight: I’m going to masquerade as the sexiest version of myself. The me I want to be but have never had the confidence to be.

6:30 p.m. Bushwick chose a nice spot. It’s Parisian bistro style. I wasn’t expecting dinner, but this is more of a restaurant than a bar. He texts that he’s running late. Of course he is. He’s a flaky artist who asks teachers if they like to fuck. Why am I here again?

7 p.m. He was a half-hour late. I’m one martini in by the time he arrives. But I will say: The man is sexy as hell! He’s got the messy hair, the dark stubble, the height, the big hands — all of it. The good news is, we laugh about our awkward first date right away. It’s a great ice-breaker, and fortunately I have no problem laughing at myself. He says he was just as embarrassed as I was, and that “Do you like to fuck?” came out wrong. Apparently, he was commenting on me talking about my “dry spell.” And he was trying to see if it was the sex or the relationship that I was missing. I buy whatever he’s selling. The point is, we were both embarrassed. I order pasta, which is very good, but I tease Brooklyn by saying my homemade manicotti is better.

9 p.m. I’m drunk! Borderline gonna-throw-up drunk, so I start pounding water. We leave the bar and start making out on the street. Before I had gotten drunk-drunk, I made up my mind that I do indeed want to fuck him tonight. I need some pleasure! He lives a few blocks away, so we walk and kiss over to his place.

11 p.m. We have sex twice. Both times were passionate and good! It’s been a year since I got laid, so I broke the seal in a positive and enjoyable way. I came both times — multiple orgasms are a rarity for me. His dick is curved and pointy, like an interesting branch. When I sober up slightly, I realize his apartment is tiny. Like, teeny-tiny. A studio that is the size of a closet. But the artwork is cool, and Bushwick himself is cool. I’ll digest the rest tomorrow.

11:30 p.m. I Uber myself home. Wisely, I didn’t drive. Before the car comes, we hug for a while at his door. He’s soulful. On the ride home, all I can think about is how I’m going to feel like garbage tomorrow.

DAY FOUR

9 a.m. At school, maybe still a little drunk. The kids are hyper. I need this day to end, and it hasn’t even begun.

11:15 a.m. My phone vibrates and I discreetly look at it. My mother. Not Bushwick. Why would I expect him to text me right now? I hope I was good in bed last night. My brain tells me that I wasn’t sexy enough. My brain also tells me I’ll never hear from him again. Welcome to my brain.

3 p.m. A teacher is talking about one of her students calling her pretty during recess, and how she didn’t know how to respond. All I can think is that no one has called me pretty in a long time. I’m probably too ugly for Bushwick …

7 p.m. I’m in bed already! I debate texting Bushwick, but I know if I do, I won’t be able to sleep until he writes back, and I really need some sleep. Today was physically painful. I suppose it was worth it, but not if this guy ghosts me. I really hope I hear from him tomorrow, less so because I like him (even though I kind of do), but just for my self-esteem.

DAY FIVE

6:30 a.m. Whisky cuddles me. Why do animals just know?

10 a.m. Today’s a new day. I’m going to devote myself to my students! I’m an excellent teacher and no one can take that from me. So, I lean into it … all day long, I’m the best teacher in the fucking world.

2 p.m. A full day and not a peep from Bushwick. I want to cry. It hurts. To be 41, still single, un-pretty, and ditched by every guy I meet. It’s really too much.

5 p.m. My emotions are a goddamned roller coaster, because when Bushwick eventually texts, “Hey girl.” I instantly feel better. Two words, and just like that, I’m healed. Lord get me into some therapy. I’m home on my couch, smiling, and plotting how to respond.

8:20 p.m. I respond, “Hey you.” Haha. So much pontification for a “Hey you.”

9 p.m. I feel good enough about our short exchange to take a shower and sleep without looking at my phone for the rest of the night. It’s Friday, and I’m always dead by Friday nights.

DAY SIX

7 a.m. Wake up, turn on my phone, and Bushwick is asking for another date! Self-esteem is bolstered. I have to feed the cat, get dressed, and get to the gym, but there’s a nice energy in the air this morning.

Noon After working out, cleaning my apartment, and doing laundry, I walk to a nearby park bench and decide to respond. I don’t want to seem too available, but tonight would be such a better night to hang out than on a school night. I write something, without sending it, that says, “Did you get your answer to the DYLTF question?” (DYLTF = Do you like to fuck?)” I can’t make the sentence flow. Instead, I tell him that I’m free tonight.

4 p.m. No response. This guy.

6 p.m. Return my slutty outfits to Zara, besides the top I wore. In returning the clothes, I feel a little sad. As if my life as a sexy, desirable woman did not last very long.

7 p.m. He never wrote back, and I’m sick of spinning out over him … over all of them. I get dressed and go to a local bar for a glass of wine and to enjoy my own company. Fuck Bushwick, but also I’m never fucking Bushwick again. I’m too old for this shit.

10 p.m. Had a nice night catching up with friends via text from the bar, and watching funny Reels of old Jerry Springer clips at home, and breathing like a normal person. I don’t block Bushwick, but I’m decidedly not interested.

DAY SEVEN

7:30 a.m. Whisky seems unwell this morning. My vet is closed on Sunday, and it’s so early in the morning that no one is picking up on their emergency line, and so I try to make other arrangements. It’s stressful. I know they’re just going to tell me she’s old and this is what it is.

12:20 p.m. I didn’t bring Whisky in. She seems to be rallying a bit. I feel comfortable enough leaving my house to take a nice fall walk. I put on my earbuds and turn on an audiobook. I’m trying to get into the Britney Spears memoir, but I’m not meshing with it.

3:30 p.m. Home on the couch with Whisky. Go on Bumble and match with a guy named Max. He’s also a teacher, but in Florida? What is he doing matching with me? He explains that he’s a New Yorker and will be home for Thanksgiving, and wants to meet some new people here. I ask if he’s just looking for a booty call. He says, “Actually, I’m looking for the real thing.” Is he playing me? I just don’t know what to trust anymore.

7:45 p.m. Max and I are texting off the app. He’s very funny. He absolutely loathes Florida and the politics there. We have a nice vibe and shorthand talking about teaching.

9 p.m. Who knows if I’ll meet up with Max or if he’ll ghost me. But I’m pretty sure a nice teacher is not going to ask me, on our very first date, if I like to fuck.

Want to submit a sex diary? Email sexdiaries@nymag.com and tell us a little about yourself (and read our submission terms here.)