Photo-Illustration: Marylu Herrera
In this week’s story, a woman tests her new relationship at an Airbnb on the beach: 32, in a relationship, Connecticut.
DAY ONE
7:20 a.m. I wake up early to the sound of waves. This Airbnb somewhere on a beach in Connecticut is exactly what I need: water views, space, light, zero city chaos. H is still sleeping — or maybe pretending to be asleep. I’m not sure. It’s been only three months together, and this is our first trip. It should be quite telling.
10:30 a.m. He’s still sleeping. Is that weird? We’re in our early 30s. It seems weird to sleep this late, but maybe I’m overthinking; I do that. I peek into the bedroom. He’s snoozing peacefully. I watch him, both wondering how I got so lucky and whether or not I trust him. He hasn’t done anything to make me not trust him, but I don’t trust men in general. My ex was a liar; the one before him was a cheater. I’m not, like, wounded wounded, but I’m a little fucked up when it comes to trusting men. H knows this about me, to some extent, but not fully. I don’t want to sound unstable to him!
12 p.m. H finds me reading on the beach — our own private beach that comes with this rental … gorgeous! He’s showered and dressed and suggests we go into town for breakfast (for him) and lunch (for me). I have to bite my tongue not to ask him when he woke up, why didn’t he come say “hello,” does he always sleep late like a teenager? Instead, I’m like, “Yup. Let’s do it!”
3 p.m. We do the cute couple-y thing: grab beach food from a crab shack, hold hands while shopping a bit, go look at the marina and kiss. H is a very easygoing guy. He’s funny, cute, pretty good in bed. We met online, and I was shocked how normal he was. It was enough to keep me interested, although I’m not sure our connection will grow deeper than it is now. I’m just not sure if he’s inherently shy and reserved or emotionally unavailable.
5 p.m. Back at the rental, we have sex. It feels more mandatory than passionate. H is a good lover. He always goes down on me. He’s got a strong dick that is always up for a good time. I usually come when we fuck, just not today. But I pretend that I do.
8 p.m. We’re grilling dinner and drinking cold white wine. Again, it’s all idyllic, but I keep waiting for the other shoe to drop. H knows none of this as I just smile and appear to be soaking in the moment. Then we get into bed to watch The Bear and go to sleep.
DAY TWO
10 a.m. He is still sleeping! Weird but okay!
11 a.m. I take some selfies and pretty pictures of our view. I’m going to post on Instagram but not sure if I should tag H. We haven’t gone Insta official yet. He’s barely on social media to begin with (he works at an elite private school, so his privacy is important to him). I work for my family business, importing gourmet ingredients from other countries, so I have no reason to be private or anxious about anything work-wise. He’s off for the summer, and I’m taking a few personal days for this trip.
12 p.m. I post and don’t tag him. Just as I do this, he arises. I call him Mr. Sleepyhead and he laughs, but I detect some defensiveness.
1:35 p.m. Same routine as yesterday. We’re in town grabbing breakfast-lunch. We’re sitting at an outdoor table talking about this area, and I stupidly say something like, “Maybe we’ll have a beach house around here someday?” I have no idea how that came out of my mouth, and he doesn’t flinch, but I regret it immediately. His response was just a little laugh. Fuck!
4:40 p.m. Sitting in our backyard by the beach, I show him the photos I posted on Insta. He’s like, “Why didn’t you tag me?” Call me insecure, but it literally fills my heart with joy when he says that. I play it cool and tell him maybe I’ll tag him next time. But the point is now I’m so horny for him that I lead him back to the house and we fuck all over the place: first the couch, then bedroom that we’re not sleeping in, and then our room. It’s, like, one long fuck session in three different scenes. In the end, I have this crazy-loud orgasm, and so does he. We’re both kind of laughing at ourselves after that. It’s the most wild our sex has ever been.
6 p.m. While he grills and I sip wine, I feel at ease, at least for now.
8 p.m. We’re showered, in bed, and watching another episode of The Bear.
DAY THREE
9:45 a.m. I’m back at the beach, reading with my coffee. H is the one who paid for this Airbnb, so I want to treat him to something nice today. I’m looking for good spas in the area and call a few to see what’s available. I book something for him later in the day. Hope he likes it!
11:45 a.m. He’s still sleeping, but I crawl back into bed with him. This wakes him a little and we start fooling around. He has horrific morning breath, but I try to work with it. My breath might not be much better after all the coffee I’ve had. Whatever. We start to fuck and something really crazy happens: He farts. We both try to play it off for a second, but then we both start laughing. He’s like, “Well, we got our first fart over with.” What is wrong with me that I find that line superromantic? We finish up fucking after that but are both too giggly to actually come.
2 p.m. I’m dropping H off at the spa place, which is in a cute nearby town. He’s super-excited. I’m glad I did this for him. As he walks in, he turns around and says, “I don’t deserve you.” He says this lovingly, but me being me, I start to spiral over it. Were they just nice, throwaway words, or was he saying that he’s a piece of shit and literally doesn’t deserve me? Was it a warning of sorts? This is how my dating brain works! It’s awful.
4 p.m. After his massage, we get drinks in town. He’s all blissed out and very quiet. I ask if anything is wrong, and he says he’s just very, very relaxed. He’s all smiley, but of course I’m nervous.
6:40 p.m. It’s our last dinner here. He’s grilling shrimp and corn while I kind of start to pack us up. Back to the city tomorrow. I call my sister on speakerphone while I fold my clothes and get our stuff out of the dryer. He can’t hear us talking, but I’m still whispering. She asks if we got “so much closer” on this trip. The answer is “yes and no.” It’s good to know we’re compatible while traveling; he never annoyed me. We have the same interests (reading) and pace when at the beach. We both like to get into bed early. But do I know him any better than before? Not really. Our conversations have been mainly superficial: work goals, financial goals, funny stories from high school and college, analyzing episodes of The Bear, etc. My sister thinks it all sounds “easy,” which is “awesome,” and I know she’s right and yet my head spins.
10 p.m. In bed, we have sex slowly and intimately. He’s the one initiating it like this. It feels like maybe this is his way of showing-not-telling me we’re closer than ever and that this is only the beginning. I hope so.
DAY FOUR
8:30 a.m. Coffee on the beach. I will have to wake him soon since we’re supposed to check out by 10 a.m.
9:45 a.m. I wake him and he tries to pull me into bed to fool around, but we really have to check out. I tell him he has just enough time to shower. We already packed everything up last night.
11 a.m. He’s still getting ready to leave, while I’m sitting on the front porch kind of brooding. I am a real stickler for time, and it feels disrespectful to be late. There could be a housekeeper waiting to come in and turn things over for the next guests. This is starting to feed rude — to me, to the owners, etc. I also really hate tardiness in general.
11:30 a.m. By the time he walks out the front door, I’m fuming, but I try really hard to play it cool. I’m physically swallowing my anger. We get in the car, put on a podcast, and start driving back to the city.
3:15 p.m. We hit some bad traffic, so it was a long drive home and somewhat awkward because I never really calmed down about him taking so long this morning — and because he’s one of those guys who cannot handle traffic. He’s yelling at no one for a good hour. It should have taken just under two hours to drive home and instead took almost four. Good thing we had so many episodes of SmartLess to catch up on; I love this podcast. H drops me off first as it’s his car. We kiss on the lips good-bye — no tongue — and I go inside, hoping my roommates aren’t home. I need some space!
6 p.m. Happily alone at home for the rest of the day. I’m enjoying the silence. I’m podcasted out. Basically staring at a wall, if I’m being honest.
10 p.m. Neither H or I text each other the rest of the day. I think we’re both just happy to be home and it’s not a big deal.
DAY FIVE
9 a.m. I’m actually happy to walk into my office today. I get to see my family, which feels great. I’m happy to be productive. I really love my work.
12:30 p.m. Right around now, while sitting at my desk, I start thinking that H isn’t for me. I just think it’s weird that we just spent four days together and I don’t feel any more connected to him in any way.
2:40 p.m. H texts a “hello” emoji. That’s the best he can do! I don’t text back because I’m busy at work and not sure how to move forward with him.
3 p.m. My sister comes into work (she’s a stay-at-home mom) to say “hi” to everyone and hear more details about my vacation. I tell her I’m on the fence about this guy. She says I need to give it more time, that he sounds nice and stable and guys like that are impossible to come by. She’s older and wiser so I listen. This leads me to text H “Hello back!”
7 p.m. My roommates and I order sushi, drink wine, and watch Love Island. I’ve known these girls for years, but they both have serious boyfriends and it feels as though these are our last days of glory together before they get engaged or married and move on.
9:50 p.m. A little sexy texting with H, but it feels hollow.
DAY SIX
8:30 a.m. My dad and I have a breakfast meeting with clients today, so I’m already in midtown at a restaurant looking professional.
10:30 a.m. I love my dad so much, and as we take the subway to the office together, I can’t help but think that H is not high quality like my dad and simply too bland. I don’t share these thoughts with my dad.
3:30 p.m. H texts about my weekend plans as today is Friday. I have a pit in my stomach. I need to break up with him. I tell him that we should get lunch tomorrow. I wonder if my text screams “I’m going to break up with you.”
7:45 p.m. Another night of Love Island with one of my roommates. She asks if I want help figuring out what to say tomorrow, but honestly I just want to watch the show, go to sleep, and try to stay calm about it all.
DAY SEVEN
8 a.m. I feel like throwing up. I’m about to dump someone who might be great and then I’m going to be single again, which is the worst. But I have to listen to my heart here: He’s not for me.
10 a.m. Take a long walk around the neighborhood just to figure out my words for later.
12:40 p.m I’m early to meet H, of course, but that allows me to sit at the table and order a drink so I loosen up.
1 p.m. The look on his face says he knows what’s coming. So I get right into it. I tell him that something about our relationship makes me anxious and it’s not his fault. I tell him that I found myself craving more closeness, but I’m not sure he can go there with me. He defends himself a little bit by repeatedly saying it’s been only a few months and that I haven’t been overly communicative either. But he doesn’t fight for me, really.
2 p.m. We never end up ordering food. Just two drinks each, then a weird hug good-bye.
5 p.m. I’ve been walking around the city for a few hours, digesting the breakup and trying to dig deeper within myself to figure out why I get so anxious with dating and how I’m going to work on it.
9 p.m. It’s a weird night at home. The roommates aren’t around. I feel somewhat sad about the breakup but relieved, too. I don’t regret ending things — not yet at least.
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