In this week’s story, an emotionally conflicted woman takes one guy to her best friend’s birthday party and goes apple picking upstate with another: 25, single, Manhattan
DAY ONE
6:50 a.m. I wake up in Axel’s massive bed … California King. With one eye open, I notice how expensive his windows look. My dad is a contractor in upstate New York, so I notice weird things when I sleep over random men’s homes. On our first date, about three months ago, Axel made sure I knew he owned his apartment and that he recently completed a gut reno. I wasn’t sure if he was showing off or proud of his hard work undertaking such a big job. Now that I know him better … he was showing off.
8 a.m. We have morning sex. I like it. He’s a “sturdy lover,” as I once heard in some TV show. While fucking, I can still smell his cologne from last night and it gags me a little, but I don’t say anything. That’s my only complaint on the sex front.
10:30 a.m. I’m home, a few subway stops away from Axel’s place in Soho. I’m taking a shower, quickly getting ready for work. I can’t say my “mornings after” with Axel are particularly glowy or radiant. I do like him, but I might like the thrill of dating him more than the man himself. He’s wealthy: family money, plus he works in finance now. He took me on my first private jet — to Vegas, to the Sphere. We always go to the best restaurants. I’m 25, living my best life, so it’s hard to back away from this shit. I guess to sum it up, he’s more of a Mr. Right Now than Mr. Right.
2 p.m. I work in the wine-and-spirits business. The goal is to open a little wine shop upstate where I grew up. I consider my 20s to be all about personal growth, career building, and life education before I move back home to start my business and hopefully settle down.
6 p.m. At the gym, watching Friends reruns on the big TV while I walk on the treadmill.
9:45 p.m. Steve calls. He’s a caller, not a texter. It’s cute. Kind of laborious, but cute. He wants to know if I like steak. Who doesn’t like steak? He wants to take me to this steak-and-jazz place for our date tomorrow. It sounds like an old-people hang. I don’t say that exactly, but he senses my lack of enthusiasm and quickly absolves himself by suggesting we should just get tacos and margaritas.
DAY TWO
8 a.m. I check my phone and see a message from Steve: “See ya tonight!!” Steve is simple, kind, and honest. He also works in the hospitality industry, which is how we met. He’s more honest than me for sure. I’ve been dating both Axel and Steve for at least two months, both with frequency, and neither know about each other. I’m fucking both of them too, albeit with protection. Neither of them have asked me to be exclusive, but both of them seem to treat me like a girlfriend. I’m playing with fire, but I cannot make up my mind and pick just one. I like both of them so much and for totally different reasons.
1 p.m. I have to take the train to Long Island today to meet with a client. As soon as I get comfortable in my seat, I respond to Steve that I’m really looking forward to our tacos and margs, but that it has to be late since I won’t get home to the city until 6 p.m.-ish.
5 p.m. I’m going to miss the train because my client insisted we go to his newest restaurant and do a little taste test. So now I’m running late for my date and very much stuffed with food.
8 p.m. From Penn Station, I quickly walk to my apartment on the East Side while calling Steve. We decide it’s better to hang out at my place because my roommates are out tonight and I’m tired as fuck.
11 p.m. After two margaritas in a can, we have sex. How do I describe sex with Steve … tender … safe … nice. He actually has a beautiful cock, but he’s so respectful of me and my body that it’s almost a turn-off. While Steve was on top of me — I happen to love good old missionary — I could see a text from Axel come in. Here I am getting fucked by one boyfriend while getting texted by the other. After sex, Steve tries to cuddle a little, because of course he does, and then I send him home. My room is small, and with four other roommates who I don’t even like coming home soon, it’s not conducive to sleepovers at all.
DAY THREE
10 a.m. We have a company meeting at a restaurant we’re affiliated with. My job is cool. My brother’s best friend owns the company, so I feel like I fit in and am valued. It’s hard to focus on the meeting because I’m feeling bad about all the lies by omission I had to tell Steve last night. Whenever he’s like, “What have you been up to?” I basically lie through my teeth.
12:30 p.m. Making last-minute arrangements for a birthday dinner for my best friend tomorrow night. My friends love hearing about my dating life; I’m definitely the Samantha Jones of the bunch. I’m also blessed that I really love sex and have no hang-ups around it. I like casual sex, meaningful sex, boring sex, rough sex. It does make it harder to choose between Steve and Axel because it’s not like one is lacking in the bedroom department. They just have different styles: With Axel, it’s more like pornographic fucking with a capital F, and Steve is more like a talented love-maker.
5 p.m. The big dilemma of the hour is which guy I should invite to my best friend’s birthday party tomorrow. I’d love to have a date there, since it’s going to be so nice. Free Champagne, passed apps. I’m going all out for my friend because she had a hard year. On the phone, I debate both guys with my best friend, and it’s kind of a lose-lose. Both follow me on social media, and there will definitely be pictures posted (if not by me, then by my group of friends), so it’s going to be hard to avoid being outed if I’m, like, making out with someone in the background.
9 p.m. I am a horrible person because I dropped a text to Axel telling him he should come tomorrow night. It’s terrible, but I chose him because I know he’ll pick up the tab and it won’t all fall on my shoulders. (It’s not all open bar.)
DAY FOUR
10:30 a.m. I’m working on Saturday, so I take today off to get ready for the party. I love throwing parties. My sister is an event planner, and my mom owned a catering company until she retired recently. It’s in my genes.
1 p.m. Manicure and pedicure. I go with neon orange for both. ’Tis the season.
3 p.m. Meanwhile, I’m texting with Steve about the weekend because we had talked about going apple picking upstate for the day on Sunday. He’s asking if I want him to find us a hotel up there, which is kind of ridiculous because my parents’ house is in the area. I like the idea of going upstate with Steve and even introducing him to my parents, but I have to get through tonight first. Too much chaos …
4 p.m. I arrive at the bar early to help set up. They’re comping a lot of this for me because I did them a favor recently with a wine vendor. The least I can do is help with the manual labor. I take off my five-inch heels and run around the place barefoot. Again, I come from a family of gritty worker bees.
6 p.m. The party starts around now. Axel is one of the first to arrive. He brought two friends with him, which I told him to do. I have a lot of single girlfriends. Axel looks hot. I’m getting used to his cologne. We kiss hello and while it feels really good, I feel a stab of guilt through the heart. Poor Steve!
7:30 p.m. I stand on the bar to toast my best friend, but first I start with some logistics. I tell everyone not to post pictures on the socials. We don’t want people mad they weren’t invited. (There goes the full-body guilt again.) I remind them to tip generously. Finally, I toast my friend, get all emotional, and then we all let loose!
10:45 p.m. The party is over and Axel is helping me help the bartenders clean up and wind down. I like how helpful he’s being. Good to know he can get down and dirty. We’re tipsy, not wasted, and I can’t wait to go home and have sex.
11:30 p.m. Such good sex! The combination of seeing him gel with my friends and feeling desired and wanted by such a successful and handsome man resulted in maybe our best sex yet. I was on top for a lot of the time … a lot of bouncing, but also some really deep kissing. I sleep over, which I don’t normally like to do — despite doing it twice this week — but I’m really tired.
DAY FIVE
7 a.m. I’m hungover but happy to be in this bed. Axel is getting dressed to go to work. He tells me I can stay for as long as I want …
10:30 a.m. I do two work calls from Axel’s because it’s so much nicer than my place. But just in case he has cameras around, I leave as soon as the calls are over, feeling self-conscious.
3 p.m. The rest of the day is mostly WFH stuff. Steve has been quiet since I kind of blew off his upstate texts. If he really did some sleuthing, there’s a chance he saw a picture of Axel and me on Instagram. There were so many people there last night; surely someone posted something. And we were all over each other at various points of the night. I don’t have the energy to research that, though.
6:40 p.m. My best friend texted me a hundred times today to thank me for last night, but now an Uber Eats delivery arrives with my favorite thing in the world: a large pepperoni pizza with a cold can of regular Coke. She knows me!
10:35 p.m. I decide to go upstate with Steve this weekend and then make a final decision about which guy I really want to get serious with.
DAY SIX
9 a.m. It’s a work day, which means visiting a bunch of restaurants and bars all over the city. It’s mostly for relationship building, which my boss is big on.
12:30 p.m. Steve FaceTimes me from his older sister’s house because she just had a baby and I told him how much I love babies and that I wanted to see her little face. She’s so cute! And it’s cute that he FaceTimed me in the first place. He’s such a kind, genuine person. I really don’t know what to do. I also feel like both guys are on the brink of asking me to label things or be “boyfriend-girlfriend” in an official capacity. It makes me feel really anxious and confused thinking about it.
3 p.m. Trying not to think about it.
4:30 p.m. Text from Axel: “Miss me yet?” FML.
7 p.m. Steve texts to confirm that he’s picking me up tomorrow morning and that we’ll be apple picking by 10 a.m. He says he’s happy to swing by my parents’ place, but I tell him “too soon!” I guess it feels mean to advance our relationship like that without knowing if it’s going to last.
DAY SEVEN
8 a.m. It’s going to be a long car ride with Steve, and I’m hoping we get to talk a little bit. I’ve decided that I need more time. I like both guys — why do I have to choose? I want to live by my own rulebook.
10 a.m. We’re listening to a Smartless episode with a boring actor. I turn it off and say something about how much I like him and enjoy being with him, but I want to make sure we’re on the same page in terms of commitment. As soon as I say this, I regret the timing. He looks … scared. There’s a lot of verbal diarrhea on my part, but I continue to assure him that we’re good, I just need him to know that I’m a slow burn with this stuff. He says he “gets it,” but he looks a little bit shook. Shit! Time to pick apples.
1 p.m. We are having a lot of fun. We rebounded from that awkward conversation. Being upstate with Steve feels decidedly lovely. This is where I want to start a family and have a career, so it’s nice to test the waters with him by my side. I like it a lot. He’s funny, kind to everyone, and so emotionally safe — but not in a bad way!
3 p.m. We have some wine and snacks before wrapping it up here. I’m trying to be present, enjoy the moment and not ask myself the hard questions about who I like more.
5:30 p.m. On the drive home, there’s a lot of traffic. It’s strange because I was once in an Uber with Axel, and there was traffic, and he was losing his shit over it. But Steve is calm. We’re playing a fun game of “Would you rather,” and I make a mental note about his easy disposition. He reminds me of my father in that way.
8 p.m. By the time Steve drops me off, we’re both pretty beat. We end up making out in his car a little bit. It feels more affectionate than any kiss before with him. It’s as if we crossed over to a new phase today, even though just 12 hours ago I was trying to withdraw from him a little.
10:30 p.m. I’m confused about who to choose, but tonight my heart feels warmed by Steve, so I stay focused on that feeling and try to fall asleep.
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