Since I last wrote, almost two years ago, much has changed. However, much also remains the same because here I am again—single as ever!—with a positively twisted desire to document my hopelessly romantic quest for love.

Have I discovered and confronted relational habits and patterns I was previously unaware of? Yes. Have I learned and pivoted and grown as a result, each time being rewarded with (slightly) better quality men, therefore proving I must be making progress? Yes! Have I ignored red flags and wasted time on a few bozos because I was weak and would sometimes accept mere crumbs of affection rather than hold out for the full, decadent meal I know I deserve because hungering for love can feel a lot like literal starvation and surely something is better than nothing? Yes, that too.

Here’s to being a lifelong learner, I suppose. In any case, I am more or less back.

After ~6 peaceful months of Monk Mode, I decided to “get back out there” around March 2025, and thus naturally redownloaded Hinge and Feeld. Now that I no longer write real-time updates like some sick freak, the following recounting of the men I dated over the last year and a half relies mostly on memory, aided in part by my Google Calendar, phone records, and Swarm check-ins. Let’s begin.

~APRIL 2025~

The Art Teacher (Hinge)

We shared three pleasant dates (1. Coffee & a stroll, 2. Movie & froyo, 3. Dinner at his place). They were all very nice but we realized on the third date that we had no chemistry. We mutually never spoke again, and I truly wish him the best.

The English Teacher (Hinge)

His profile photos made it hard to fully decipher his face, which meant I was rolling the dice on whether or not he was cute. He ended up being less attractive than I was hoping for and, unrelatedly, a very mediocre dinner date ensued. To make matters worse, I was forced to pay half when the bill came. My fault for agreeing to dinner on a first date! (Rookie mistake, smh. This monk was clearly out of practice.) However, the restaurant was tasty and I’ve been meaning to return.

The Artist who built a tiny house (Feeld)

When I arrived at the coffee shop, he appeared older than I had expected/hoped, so we weren’t off to a great start. However, we got coffee and proceeded to embark on a semi-treacherous hike that gave us something else to focus on. Very nice guy, but another one-date-only.

The Triplet (Feeld)

From the very beginning, I could tell he was a fuckboy. And yet? He was absurdly persistent (and funny and scary smart) so I eventually agreed to meet him. It also turned out that we have the same birthday (I’m exactly 3 years older), so how could I resist? (He joked that if we ended up together, we’d have to have a 4-way birthday celebration with his triplet sisters. Can you imagine anything worse?)

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On March 23, I met the Biologist for coffee.

On April 5, the Biologist and I escaped an escape room, ate hot dogs, and then never spoke again.

Later that night, against my better judgement, I reactivated my Feeld account.

On April 6, I matched with a Swedish tattoo artist who was visiting/working in LA for …

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While I was in New York, the Architect texted me a fair bit and made it abundantly clear that he wanted to see me as soon as I got back to LA. How refreshing!

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(BTW I’m writing this from a middle seat on my flight to NYC and I can only assume my seatmates are surreptitiously reading as I write. I do hope they enjoy.)

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1. How come you didn't get discouraged after he [Sexter] avoided the date so many times? 

   1. I was definitely discouraged, and also suspicious. However, I also believed him when he told me that it was mostly because he was exhausted at the end of every day/week due to a commute that has him driving over an hour each way (which sounds fucking awful). I had also peppered him with a lot of questions and discovered that he’s a fellow introvert, which made it even more understandable that he needs a lot of alone time to recharge (which he doesn’t easily come by because he lives with his best friend). Basically, he had really good excuses, and I was choosing to be graciously understanding.

2. Also how come you didn't drop him when he said he didn't want to leave the house / or didn't confirm the movie date until the last hour...? Maybe it's an old school European in me but I personally would feel that's disrespectful and not worth my time, but you're making me feel like maybe I'm wrong?

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With that in mind, I decided to try Feeld—an “open-minded” dating app that’s more sex/desire/kink-forward. It’s a lot of ethical non-monogamy (ENM), couples looking for thirds (aka unicorns), and a dictionary’s worth of sexual acronyms. (For a taste of what you can expect to find on Feeld, I’d recommend googling the following NSFW acronyms, adding ‘kink’ to your search when necessary: CBT, CNC, and—my personal favorite—ABDL.) Instead of scrolling on Instagram, I sometimes open the Feeld app purely for entertainment purposes. Here are some examples of totally normal profiles:

In addition to being my new favorite entertainment service, Feeld has also helped me meet a handful of nice men. Here are all the dates I’ve been on recently:

• Professor - My first app date in a very long time, let alone my first Feeld date. He was sweet and funny but only in town for his Winter Break. We got coffee and politely kissed goodbye.

• Married Man (ENM) - We met up for coffee and I basically interrogated him about polyamory. He is a true gentleman, but I think we are both skeptical about our romantic chemistry. (Also, it just feels mentally easier to date single guys??)

• Architect - We’ve been on two dates (coffee, Ethiopian food) and I really enjoy talking to him. However, no moves have been made and I wonder if we should just be friends.

• 46-Year-Old - We walked around and explored a big park for a few hours. He brought snacks and games for us, and even knows about permaculture, but I have yet to be convinced of our chemistry.

Then, a couple of hours later (that’s right, I went on two dates in the same day1 and was surprised to realize I had never done that before) I went out with…

• Sexter - After talking for 3.5 weeks, we finally met at our local movie theater to watch Anyone But You (and eat an obscene amount of popcorn) and then got drinks at a tiki bar afterwards. Here’s a bit more context on him…

In mid-January, about a week into actively using the app, I matched with a very attractive and seemingly normal (in the context of Feeld) guy. He immediately made me laugh, and then one thing led to another (??) and suddenly we were sexting right there in the app (which is somewhat encouraged by its feature of timed, disappearing photos. Despite what you’re probably assuming, I did NOT send any photos of myself!). Having never sexted before, I took my two orgasms as evidence that this was perhaps an above-average encounter. The next night, a Thursday, we sexted again. He didn’t message much during the daytime, but the app is quite buggy and doesn’t actually notify you if you have new messages, so I chalked it up to that.

That weekend, I met the Professor and the Married Man. While they were both lovely, the banter and chemistry didn’t come close to what I had—albeit via a screen—with Sexter. By the end of the weekend, shocked that he wasn’t asking me out as fast as these other guys (wasn’t he trying to fuck for real?), I asked Sexter if he was interested in meeting (he said yes) and gave him my phone number. We texted a bit for a day or two (nothing beyond PG-13), but he would take hours to respond, often dropping off in the middle of the conversation. I was beginning to feel the all-too-familiar WHY-ISN’T-HE-TEXTING-ME anxiety reminiscent of fuckboys past. Not only was he not engaged in our conversation, but he also wasn’t even trying to sext anymore. Confused and disappointed, I could only assume he had lost interest and moved on.

After a week of not hearing from him (I refused to put in any more effort), I decided to unmatch him on Feeld because I felt he no longer deserved masturbation access to our steamy chats and my not-even-that-steamy profile pics. Having recently been unmatched by someone else, I knew that the app notifies you when someone unmatches (insane feature, if you ask me). I hadn’t saved Sexter’s phone number (I typically don’t until I really like/know/trust a guy) and I had already deleted our paltry text thread, so I now had no way of contacting him even if I wanted to. Boundaries! Empowerment! Feminism!

Well, the next day (a Friday morning), I woke up to a fresh text: “I know my silence might suggest otherwise, but I wouldn’t like to be done talking to you”

Confusing, right??

Me: Well that’s confusing

Him: I know it is. I’m sorry about it. If it’s too confusing to be worth it for you, I can understand that

Me: It feels like there’s something you’re not telling me about your availability.

If I hadn’t already stalked you online,2 I’d be convinced you’re a catfish

You’re the mysterious elusive one here

Him: I almost wish I was a married catfish just to keep the excitement alive

Reality is far less intriguing

[I reeeally didn’t intend to get into this much detail, but I also believe that context is essential. That being said, I’m gonna throw the rest of this behind the paywall. But before I do, I wanted to make a little announcement that I’m going to be using this inconveniently enthralling situation (spoiler: our date was great and I like him! Ack!) as an opportunity to commit to a consistent writing practice. In the weeks to come, paid subscribers will receive weekly reflections on the various emotions, triggers, insecurities, and hopefully revelations that come up for me during this time. Let’s see how this goes!

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While I mostly just hit ‘shuffle’ on My Shazam Tracks, I also frequently listen to the playlist I created during a rainy weekend of romantic vision boarding (right before Sauce Man and I broke up).

When it came time to commit the collage to Mod Podge, I wanted to imbue the glueing process with as much love and intention as possible. So, I made a playlist of songs that I felt communicated the type of relationship I was trying to manifest—an auditory vision board, if you will.

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Instead of waiting who-knows-how-long to write about something exciting, I figured I’d bridge the gap and share the few tame Interactions With Men I’ve had in the past 6 months:

(1)
In August, a new man friend cooked me din…

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I finally put my 16-month situationship with Goodtime Guy out of its misery and am officially single again! (I still think he’s a lovely person, but we are not right for each other.)

Overall vibe:

The (very) long of it:

As previously mentioned, I’d been having second thoughts about Goodtime Guy for a while. For the majority of the time I was abroad, I felt our communication wasn’t up to the quality or frequency I’d want in a “real” relationship. On one hand, I felt light and independent, not worrying about when I’d hear from him. But on the other hand, it felt odd that neither of us was clamoring to talk all that often. It sorta just seemed like we didn’t have much to say, or that we didn’t really miss each other. When we did talk, I started to notice how differently we approach The Big Things, like career, lifestyle, and money. 

Then, after my permaculture design course blew my mind open to the possibilities of what my life could look like, I felt motivated to start taking bigger steps toward the future I wanted. While Goodtime Guy and I share a similar idyllic vision of moving abroad and having a home with a garden and creative spaces, it was becoming clear that I’m much further along on that path than he is—and I didn’t want to wait around for him to maybe catch up. 

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Shortly after arriving at my mom’s in LA, I booked my flights to New York (Dec 29) and Portugal (Jan 7). But then, it turned out that Goodtime Guy was coming out west for work and would be in LA for two non-consecutive nights while I was there. His trip cut mine perfectly in half, so we only went ~12 days without seeing each other. When he got to LA, I took him out for Mexican food and then slept over at his hotel, and in the morning we had breakfast with his coworker. When he came back into town, we had a double date with some friends of his—who were not shy about PDA—before having another fun hotel sleepover. (In case you’re wondering, I told my mom that “my friend [name redacted]” was in town. I don’t know what she thought—or if she even cared—about me spending nights with a “friend.”) Before he left, we decided that I would indeed stay with him (as opposed to my friend’s empty apartment) during my upcoming 8-day layover.

January

Goodtime Guy and his roommate threw a spectacular New Year’s Eve party, and I met his sister. We all danced, wore wigs, and I stayed up until 3:30am! The next few days were largely uneventful, until I had a meltdown on the morning of Jan 4th. I was freaking out about my trip and all the uncertainty that came with it. As I wept, he consoled me and reassured me that everything would be fine; he praised my bravery and encouraged me to feel excited about my adventure. He legitimately made me feel better, and I could no longer ignore The Feeling that had been slowly growing over the past couple of weeks. It was extremely bad timing, but for the sake of authenticity, I felt I had to be honest…

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I’ve mentioned this before, but my most depressing day of every year is whenever I have to fly back to the New York grind after 1-2 weeks of sunny, silly, San Diego bliss. As I texted Goodtime Guy upon arrival at JFK, my melancholia was obvious. He said it sounded like I needed company, and I didn’t disagree. It was the Sunday of Labor Day Weekend and he was at a friend’s barbecue; he said I could probably join, but I was in no mood to mingle with strangers. Having been forsaken on this fragile day in years past, I felt very cared for when he showed up later that evening to hang out with a lightly-catatonic Emily. 

The next day, I assumed he’d go home after breakfast and I’d have the rest of the day to recharge. As we walked around in search of sustenance (my fridge was empty and most places were closed for the holiday), he acknowledged my lackluster demeanor and said, “I know you’re not stoked to be back but I’m glad you are.” Although that made me smile, it wasn’t enough to lift me out of my darkness. After we ate, despite my very quiet and unentertaining mood, it seemed like he had no intention of heading home. And because I’m a people pleaser who struggles to notice—let alone express—my immediate needs lest they offend or disappoint the very sweet person before me, I didn’t say anything. Did I regret letting him come back to my apartment, where all he did was fall asleep? No... But did I regret squandering the opportunity for alone time (after having had only 3 days to myself during the 3.5 weeks I was away) before the rush of reality revved back up? Absolutely!

Additional background on my mental state during this time:

For the previous ten months, I had known that I’d be leaving NYC at the end of 2022. But it didn’t become “real” until I returned home from my trip and told my landlord that I’d be moving out in 3 months. Now that I was back, with an unimpeded view of my impending exodus, it was hard to focus on anything else. To masochistically unsettle my life even further, I had recently niched down my career to focus exclusively on naming, and had launched my new brand & website only a couple weeks prior. So while I was trying to get the word out and stir up some projects, I also knew that I could only reasonably dedicate a fraction of my energy to paid work when the task of selling-or-packing-everything-I’d-accumulated-over-the-last-decade was pressing down upon me. Needless to say, my resting state was extremely anxious. Plus, because I’d taken most of the year to reflect on and restructure my professional life, I’d been living off of my now-dwindling savings and had recently decided that therapy was a luxury I could no longer afford. LIFE WAS STRESSFUL, and I shouldn’t have been surprised when it started to manifest in my physical health (more on that soon)—which, of course, only compounded my anxiety. What I’m saying is: I was simply trying to stay afloat—emotionally, physically, financially—and Goodtime Guy was not a high priority. Looking back, it would have helped if I’d been better at listening to myself and setting boundaries, but ya live and ya learn!

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Greetings!

I am well aware that it’s been an extremely long time since I’ve sent an update. I was in the midst of a developing story—which you will read about now—as well as the complete overhaul of my entire life. *laughs/cries simultaneously* I actually started writing this in July/August, but things kept happening and it felt easier to simply live my life rather than analyze it for documentation.

Thank you for your patience. To those of you who were decidedly not patient, thank you for being a ravenous fan.

<3 Emily

Act 1 - New York

Ahead of my infamous Seattle trip, I had obviously forecasted the potential best and worst case outcomes. Best Case: my feelings would be reciprocated by Rotary Boo and we’d somehow live happily ever after. (LMAO) However, that would’ve also likely triggered the Worst Case: no more Goodtime Guy hookups. Well, everything happens for a reason and, as you already know, I got to continue having the Best Sex of My Life. Hooray!

***

Side Note: A few weeks ago, I was struck by a very random urge to surreptitiously check in on Rotary Boo. While he has zero social media presence, I was able to employ my superior sleuthing skills to discover that he apparently… Has. A. Girlfriend! Lolzzz. It’s also unclear if he ever went on that solo adventure he was dreaming about; assuming he didn’t, I actually feel turned off by his lack of follow through. Disclaimer: we are not in touch, so this is all 100% speculation on my part! In any case, I feel wholly indifferent about his relationship status and I wish him the best in life. Now, moving on…

***

After I returned to New York in May, Goodtime Guy and I began hanging out more frequently. While sex was still the main reason we got together, it was no longer the only reason. For the last year, I’ve felt incredibly lonely and disconnected, so it was really nice having someone I could count on to regularly spend time with. By the beginning of summer, I had privately decided that Goodtime Guy and I had officially graduated from “fuck buddies” to “friends with benefits.” 

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Those first few post-Seattle days were tinged with a mild misery. Back in NYC, it felt like I no longer fit. I had been feeling this way for months, but now it was unignorable. Even my cute & cozy apartment felt oppressive. Also, I obviously missed Rotary Boo. My feelings for him were finally certain, but everything else felt foggy and unpredictable. This was only amplified by the fact that he was now basically unresponsive. All I could do was cling to the knowledge that we would talk on the phone at some point that weekend.

We ended up scheduling our call for Saturday afternoon. In the meantime, Goodtime Guy invited me out to a jazz bar on Friday night. I met up with him and his friend, but was feeling distant. Because we are each other’s exclusive sexual partners (we haven’t used condoms in months—my IUD is finally being put to use!), I knew I needed to tell him that I’d had sex with someone else. After a pretty fun night out, Goodtime Guy and I went back to his house. I told him I couldn’t sleep over because I had a workout class in the morning (but also because I couldn’t bear the thought of spooning the night away with someone who wasn’t Rotary Boo). Sitting on his bed, about to commence our Usual, I said I had to tell him something: 

Me: I had sex with my friend while I was in Seattle.

GG: Ok…

Me: We used a condom! But I just wanted to let you know.

GG: So… do you want to use a condom now?

Me: I don’t think we need to? But it’s up to you.

GG: ...I think we’re fine.

I think he was expecting a scarier conversation. When I asked if there was anything else he wanted to say, he said, “well, I think I went on a date while you were gone?” (Confused, I asked what that meant and, long story short, I don’t think it was a date.) With nothing else to discuss, we started to makeout, although I didn’t think I’d be able to get into it. Whenever my brain tried reminding me that this was not the person I ~loved~, I flicked the thought away. Gradually, I felt myself shoving my feelings for Rotary Boo into another area of my mind and locking the door behind them so they wouldn’t see what was about to occur. 

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Wednesday, May 4th 

He was picking me up around 7pm. Instead of waiting inside my Airbnb, I decided to walk around the neighborhood until he arrived. I told him to call me when he was nearby, then meandered down a street I hadn’t yet explored. I was admiring the fancy Capitol Hill homes when I stopped to read a poster on a street pole.

“Emily?”

I turned around and there he was, looking just as shocked as I felt. Apparently, he’d arrived early, parked a couple blocks away from my Airbnb, and had been waiting for me to text that I was ready. Somehow, I beat him to the punch and serendipitously stumbled upon his parking spot. We laughed and hugged before getting in his car, stunned and amused by the surreal synchronicity of it all.

Still in shock from our abrupt meet-cute, I felt flustered as we picked up food and drove to Discovery Park. I was overstimulated, both by my new surroundings and the novelty of sharing airspace with him. It wasn’t awkward—we picked up right where we’d left off—just sensory overload. 

Inside the park, we sat on a log and looked out at the water, eating and catching up about our respective trips. I could feel his eyes on the side of my face. I was so used to staring at the walls of my apartment while we talked on the phone, that I had to make a concerted effort to return his gaze. Eye contact felt radical. 

By the time night fell and we left the park, I had adjusted to being in his presence. Back in his car, we drove to Bhy Kracke Park, where we had a pretty spectacular view of the city. We got out and sat on a low wall. Behind us was a carful of teenage boys doing teenage boy things, so romance didn’t cross my mind. After chatting outside for a bit, we went back to his car so I could drink some water. Meanwhile, another car pulled in two spaces over from us. From my passenger-side window, we spied on this vaping, laptop-using weirdo, imagining that he must be the father of young twins and this midnight escape from the diaper cycle was his only chance to work on his passion project—but I digress. By now, Rotary Boo was leaning all the way over, craning to see the guy beyond my head. And his hand was on my knee. When I turned back toward him, he didn’t move away. Instead, after a moment, he kissed me.  

I wasn’t expecting it, but I was also relieved. I literally thought to myself, “Thank god he kissed me so I didn’t have to verbally express my feelings.” Ha! (It also felt a bit odd to be kissing someone new, having grown so accustomed to Goodtime Guy. Not bad, just different.) We stayed there for a while—“parked”—making out in his car above the beautiful vista. It was some real teen movie shit and we acknowledged that, indeed, we felt like teenagers. He drove me home around 1am and we kissed goodnight. 

Thursday, May 5th

It didn’t dawn on me until the next day that we’d basically been on a date the whole time. He’d paid for our food, chauffeured me to various scenic lookouts, and put the moves on me in his car. Had we talked about our feelings at all? No, but at least we confirmed that I wasn’t in the friend zone. That was good enough for me!

Friday, May 6th

I was out and about when he texted me around noon:

“Heyyyyy hope you are finding some cool stuff today even tho it’s wet! I’m gonna stop working at 5 wanna come by my place? I can make us some tea and get us Thai food later 🤠”

The sun eventually emerged, so I walked the 45 minutes to his house. I was excited, but still a bit nervous. His place was cute, and the boat phone was even more beautiful in person. He gave me a tiny bobble-head turtle he’d picked up in Mexico and a collage-y card he made me. We chatted on his couch for a couple of hours and then walked to dinner (I paid!). It was raining when we left, so we huddled under my umbrella for the 15-min walk back.

Back on his couch, we started to make out. As things progressed, it felt slightly weird that we still hadn’t addressed the small herd of elephants in the room/my brain (i.e., “Soo… we have feelings for each other, right?” “What does this mean moving forward?” “When do I mention Goodtime Guy?”). But I was enjoying myself, and wasn’t about to interrupt the fun to initiate a serious conversation. BO-RING! We could deal with all that later. Instead, I was focused on getting naked and moving to the bedroom. ;)

Saturday, May 7th

After waking up and doing it again, we ate our leftovers for breakfast. Needless to say, I was flying pretty high. Our connection seemed to be just as easy and fun in person (both clothed and nude) as it had been over the phone. He had a work call later that afternoon, so we went for a walk and found somewhere sunny to sit and talk…

His lease was up at the end of July and he was thinking about not renewing. He loved his Seattle community and underpriced apartment, but was contemplating a more adventurous, nomadic life while he had the chance. Unattached for the first time in a long time, he wanted to explore his various whims and had some cool solo excursions in mind for Fall & Winter. It all sounded very exciting and inspiring—not to mention extremely appropriate for his Saturn Return (occurring in Aquarius and his 7th house of relationships, no less). 

At the same time, I was starting to feel overwhelmed and emotional. He was so excited to be in complete control of his life, to not have to consider a partner in any of his decisions. I, on the other hand, had been yearning for the opposite. Ever since moving to NYC almost a decade ago (and consequently being dumped for it), I have governed my life with complete autonomy. It’s both a blessing (I do whatever I want, whenever I want!) and a curse (what the fuck do I want???). Well, the one thing I do want is a partner; someone with whom to co-create a life that’s bigger and better than anything I could possibly imagine on my own. So, in planning to move back to the West Coast but not knowing exactly where, I had sort of been assuming that if things went well on this trip, the decision could be made for me. But it was now clear that that definitely wasn’t happening, and I was once again saddled with the annoying responsibility of figuring out my future on my own. UGH! (However, I was a little relieved to cross Seattle off my list of options—I liked Portland more.) 

To be clear, I can’t say that anything Rotary Boo said came as a total shock. Dreaming up out-of-the-box artist lifestyles was one of the first things we bonded over back in January. In fact, when he was initially reading ABCDEFG and messaging me compliment after compliment, he had said:

“I really appreciate your writing tho because being single now I just want to make sure I can focus on what I want/need because that’s never been a thing and it seems like that’s what you do.” 

The irony stings. 

The other reason I was getting emotional was because I really liked him, and it was apparent that his feelings weren’t nearly as strong. As I attempted to articulate all of this, I, of course, started to cry—less out of sadness and more due to my physical aversion to vulnerable self-expression. I’m soooo resistant to putting myself out there (Scorpio Sun, Venus, and Mercury ftw) that in order for my True Feelings to escape the bodily bunker I’ve trapped them in, I assume they have to melt themselves down into an embarrassing liquid and seep out through any available orifice—usually my eyes, nose, and sweat glands. (Imagine my emotions are like Alex Mack morphing into a silver puddle to slip under doors). When I asked if he had a tissue (he didn’t), he suggested I wipe my nose on the corner of the flannel he was wearing. I hesitated, but he insisted, saying he needed to wash it anyway. Thus, for the duration of this outdoor conversation, he encouraged me to BLOW my nose into the corner of his shirt. It was both very sweet and supremely disgusting. 

Overall (and in spite of my facial leakage), it was a productive conversation, albeit a bit convoluted and abstract at times. I told him I liked him a lot. He said he liked me too but [see above]. Then, we started pontificating about relationships in more general terms. We agreed upon the importance of independence in a partnership, and how both people deserve the freedom and support to grow, explore, and change. Obviously, this requires healthy communication. We pondered alternatives to the traditional model of a partnered lifestyle (e.g., sharing a single home/room/bed every night for the duration of a 30-year mortgage) and wondered what it could look like to live more seasonally, in different locales, sometimes together and sometimes independently. (As someone who adores having my own space, I’m intrigued by the idea of being in a committed relationship that isn’t necessarily defined by constant physical proximity. More on this in my next email!) It also helped me verbalize the idea that I want to anchor myself to a person/relationship/connection rather than to a particular city, home, or lifestyle. 

We also talked about my next moves, post-NYC. Knowing how much I love the beach and warm weather, he asked why I was even entertaining Portland over my lifelong lust for San Diego. This alone set off my eye sprinklers. Why not go all in on my beach bum dream? San Diego will probably be underwater in a couple of decades anyways, so I might as well live out my surfer girl fantasy while there’s still time!

As we walked back to his house, I told him that our conversation made me feel better about the fact that I’d been casually sleeping with someone else this whole time. He said that made him feel better, too. (So, I secretly celebrated the fact that we were all in favor of me continuing to have guaranteed orgasms with Goodtime Guy. :)) 

Back at his house, we continued talking, but I felt like I was overstaying my welcome. Our honesty was great, but I was reminded of all the Beginning-Of-The-End conversations I’d had in the past (see: Mr. Pineapple, Neighbor Boy, Diet Coke Dealer, Sauce Man), the ones where I’d been deluded into thinking there was still hope. I felt confused because we were still talking about visiting Whidbey Island while I was there. So I did still have hope—for exactly what, I don’t know. Making myself as compact as possible on the far end of the couch, I felt myself closing off as I entered self-protection mode. I was experiencing a myriad of emotions and it was all very overwhelming. This is probably why I could not stop crying. The waves just kept coming and it was all quite embarrassing. But shoutout to Rotary Boo for not batting an eye at how much of a weepy mess I was. I’ve never had someone be so unphased by so much ugly crying. My feelings and I felt very safe.

He eventually drove me back to my Airbnb around 3pm. We had obviously talked about A LOT of stuff, and I told him I was excited to journal it all out. Parked outside, I apologized for making things weird that day. But he said it hadn’t been weird at all; he was glad we talked and that he’d been able to articulate some of the things he’d been thinking about. He said he would text me in a few hours (after his postponed call with his work friend) to let me know whether we should go to the island the following day (Sunday) or Monday (my last day). We kissed goodbye—which was equal parts surprising, reassuring, and confusing.

~~INTERMISSION~~

When we got back to his place (and I finally got some tissues), I checked my phone and saw a text from Goodtime Guy:

“Wanna go to Mexico? Planning a lil getaway to Sayulita May 29 - June 6”

WTF?! My booty call was inviting me on a TRIP?? This made me even more confused! Later, I was comforted to learn that he’d also invited our mutual friend (but only after inviting me first). I guess I can’t blame him for wanting vacation sex, but I couldn’t go, regardless.

~~END OF INTERMISSION~~

Back in my Airbnb, I sat down for some 4pm Morning Pages. As my thoughts flowed freely, so did the tears. I was overwhelmed by every emotion under the sun. I felt inspired and activated by Rotary Boo’s outlook. I was devastated that our timing was so off. I was steeped in uncertainty, unable to envision what my life might look like in 6 months. And I still couldn’t stop crying! What the fuck was happening to me?? I was genuinely excited for him to lean into the soul searching that a Saturn Return demands. I wanted him to explore and find his way! But I also hoped that way might eventually lead back to me… But even if it didn’t, I still wanted the best for him. Really! Because I… <gulp> loved him? Fuuuuck. Was that crazy? Or did it just feel crazy to finally be telling myself the truth? 

To be clear, I wasn’t dick-matized (the sex was really fun but I hadn’t come). I once told him I loved the way my brain worked after rubbing up against his, and this was still true after our intense afternoon. I just loved being around him, talking with him, everything. But I also wanted him to have all the experiences he was talking about. I wanted him to be free to explore and grow and do whatever he wanted to do with his life. If that’s not love, I don’t know what is. 

The flood gates were officially open and there was no going back. I needed him to know exactly how I felt. I didn’t want to make him feel pressured or guilty, but I also couldn’t hold this in any longer—that wouldn’t be fair to me. However he reacted or responded would be on him. It’s not like I was expecting him to feel the same way (I already knew he didn’t) or “choose me” after sowing his wild oats. I couldn’t possibly expect that. But I could still want. I could still hope. I could put myself out there, heart on my sleeve, and actually do something about my feelings. If it doesn’t work out, it doesn’t work out. I knew I’d be okay—I’ll always be okay. But at least I’d know I tried, that I went after the thing/person I cared about most. I would do the scary thing!—while remaining unattached to any particular outcome. <Insert Exhausted Sigh>

After four pages of manic journaling and a few hours of further emotional processing, I decided I needed to get clarísimo on everything I wanted to say. Considering what a struggle it had been for me to communicate earlier that afternoon, I ended up corralling my thoughts into a short letter that I planned to give him at the end of my trip. With my feelings finally crystallized, I felt calm aka emotionally spent. He texted me before bed to say we should go to the island on Monday (my last full day). Knowing I’d have the next day to myself, I fell asleep. 

Sunday - May 8th (my half-birthday btw :))

Upon waking, the journaling and crying continued—LOL. My chest literally hurt. But it didn’t feel like my heart was breaking (been there, felt that). Instead, it felt like it was cracking wide open. I’ve blathered on about being OTL, but this was when I realized that OTL is a two-way street. It isn’t just about being open to love coming in; I had to be equally open to love pouring out of me. Much like the Grinch, it felt like my heart was growing 3 whole sizes to accommodate all these new feelings and pathways—and it was fucking exhausting! #eclipseseason

After calling my mom for Mother’s Day and fiiiiiinally reaching the bottom of my tears tank, I stepped out into the rare Seattle sunshine for a much-needed stoner stroll. With the exception of my sleeping hours, I had basically been crying for 24 hours. My puffy eyes and I were grateful for sunglasses-weather.

I was in a nearby park, sipping coffee and enjoying an emotional support pastry, when I saw that Rotary Boo had texted me:

“Heyyyyy I’ve been doing some work but it’s nagging me that it’s so FUCKIN nice out and my buddy is still silent… I can’t help but think just hit the island today it’s only like an hour drive and suns up till 9 🤔  Are you neck deep in a 6 hour Seattle guided tour?”

I was mildly stoned and moderately puffy. I wasn’t expecting to see him until the next day… but I also didn’t have anything else on my agenda, so we planned to meet in an hour. (I’d like to thank makeup and a frozen spoon for helping me look halfway normal.)

Things felt slightly awkward at first, but maybe that’s because I was still a little high. By the time we reached Whidbey Island, things (including my brain) felt normal again and we proceeded to have a spectacular day. We frolicked on a beach, devoured massive ice cream cones and shared a hot dog, and talked on a cliff at golden hour. He asked me how the previous day’s journaling went. I didn’t mention my emotional breakthrough or the letter I’d written (which I had in my bag), but we talked about our connection as well as our very bad timing. Thankfully, I knew there was no way my body could possibly generate any more tears. I made it clear that I didn’t want to hamper his plans, and he continued to make it clear that he’s not ready for a relationship. (On our drive, he had said he’s not great at maintaining long-distance relationships, platonic or otherwise. While I “believe people when they show/tell you who they are,” I do think our call log would beg to differ. *shrug*) It was quite the mature discussion, if I do say so myself. It actually felt liberating to acknowledge that we had no future to speak of, and I quietly decided to make the most of our time together. 

We drove to one final spot, where we hiked up a grassy hill above the water. As the sun set, we laid amongst the wavy, golden grass, beneath a half moon that looked cut out of the slowly-darkening sky. It was indescribably beautiful. We talked, we kissed, we soaked it all up. When two bald eagles soared past, just a few feet in front of us, I knew we were in a goddamn movie. It was a magical, beautiful, fun-filled day that I will cherish for years to come—regardless of whatever happens. 

We drove back to Seattle in the dark. On the ferry, I let him read what The Pattern app says about us. When we got back into the city, he asked if I wanted him to drop me off at my Airbnb or keep hanging out at his place. It was 11pm, and I obviously chose his place. We made some tea and eventually went to bed. Third time’s a charm, meaning I came. :)

Monday, May 9th (my last day)

In the morning—after mentally memorializing our final moments in bed together while he slept (Hi, my name is Emily and I’m a CREEPER)—we wrote our morning pages and ate breakfast. We decided to squeeze in one last dinner together, so I took my letter with me when he dropped me off.

Later that evening, we feasted on ramen before going to the pinball/arcade bar he had told me about when we had first started talking. We were having so much fun, but it was soon 11:30pm and my flight was at noon the next day. Arms around each other, we walked back to his house. We talked about what a fun time we’d had together, knowing the end was near. Around midnight, desperate for more time together, I asked if he wanted to hang out with me while I packed. I don’t think either of us wanted to say goodbye just yet, and he said yes (phew!). On our way out, I told him I had written him a little letter, which I left next to the boat phone—#cinematic. When we got in his car, he kissed me and reiterated how fun and easy it had been hanging out all weekend. During the short drive to my Airbnb, we finally talked about how anxious we’d felt leading up to my visit. I had been nervous about our in-person chemistry, comparing our months of phone calls to Love Is Blind.

He chilled on the bed while I flitted around packing. When I was done, we kissed and cuddled and savored our final moments together. We belabored how much fun we’d had while appreciating the unpredictability of this thing we call Life. Fiiiiinally, just before 2am, we knew it was time for him to go. As we reluctantly pulled ourselves apart at the door, we planned to talk on the phone later that week. 

Tuesday, May 10th (SEA → JFK)

I felt content and hopeful as I left for the airport. (And no, I didn’t cry!) Even though the future was 100% uncertain (I suppose it always is), I had enjoyed a wonderful few days with Rotary Boo. It confirmed everything I’d felt over the phone, and more. Sure, I wondered if we’d still talk as much moving forward, and I had no idea when (or if?) we’d see each other again, but that didn’t change how I felt about our time together. I had done and said everything I wanted, and I was heading home with zero regrets. If this was all the time we ever got together, so be it. No matter what the future held, these five days had been worth it. 

Next time on ABCDEFG:

Stay tuned for a few more updates on Rotary Boo & Goodtime Guy, plus insightful reflections on how I’ve been feeling since I’ve been back.

In the meantime, here’s that love letter I wrote:

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