For your appetizer, please enjoy a few minor updates that I forgot to mention:

Back in March, on my first date with Not My Husband, the bartender turned out to be none other than Alabama Boy. Despite him being masked the whole time, his incredibly unique first name sparked my memory and led me to creep on IG, where I confirmed he is not only the bartender, but owner of the bar I’ll obviously never revisit. 

In August, near my old neighborhood, I was sitting outside a coffee shop with my friend, when I saw Neighbor Boy in line for a coffee of his own. Reluctant to be recognized myself, it was challenging to confirm his identity—but I am 97% sure it was him. He has a dog now, which I sincerely hope is boosting his mental health. 

In July (I’m aware this is out of chronological order), one of the Zoom dates I had in April resurfaced, apologetic for never following up and asking if I’d like to meet in person. Our Zoom interaction, while less than memorable, had been perfectly enjoyable, so I agreed to an in-person version. Despite a small red flag pertaining to how he basically chugged 4-5 beers while I nursed 2 (granted, I’d come from client drinks and had told him to catch up), the IRL conversation was equally enjoyable. Nonetheless, I told him I felt called to spend my energy elsewhere.

However, in the words of Carrie Bradshaw, “I couldn’t help but wonder…” Was the lack of sparks a sign of a healthy, comfortable connection, or am I simply a charming conversationalist who can have a pleasant time with anyone? What’s the difference between feeling comfortable and at ease with a guy, and feeling not romantically interested? Where’s the line between being OTL and “settling” for any decent human?

Now, for your main course:

I was recently set up with my cousin’s wife’s friend’s fiance’s friend (CWFFF) for a blind date. He was given my phone number and we texted to make plans. I informed him that I’m taking a break from alcohol and don’t mind if he drinks, but he was surprisingly into the idea of a sober date and we planned to get dinner at Via Carota. Though he came highly recommended, the idea of meeting a complete stranger for a booze-free, cloth-napkin dinner made me nervous. I was going to have to be my metaphorically-naked self—which is historically scarier than being my literally-naked self. Knowing I wouldn’t be chaperoned by alcohol, it felt like I was going on my very first date again. Thankfully, he turned out to be kind, funny, and smart and we talked for 5 hours. We hugged goodbye, confirmed we both had an enjoyable evening, and made plans to hang out again in two weeks. We texted occasionally, casually, and I experienced zero anxiety (likely because I’ve been too distracted by work anxiety).

Last night, for our second sober date, we got pho (I paid this time!) and then made the spontaneous decision to snag the last two spots in a nearby escape room (and smoke a tiny bit of weed). Afterwards (we all escaped), he walked me to the subway station and told me he had a great time and would like to see me again. I told him I had a good time too, but was only feeling a friendship vibe so far. In an unprecedented display of honesty, I shared what I assume is my unkind habit of continuing to date someone while I wait to see if my feelings might change or grow. I told him I didn’t want to waste his time, but he was very understanding and said he still wanted to invest more time in getting to know each other. Mildly stoned and trying very hard to find the right words, I’m not sure how I came off. When he asked if I wanted him to stop contacting me, I said no. But when he asked if I wanted to hang out again soon, I said I didn’t know. We obviously didn’t kiss, but hugged goodbye before I got on the train. 

I rode home feeling confused and sad. I thought about the chemistry and excitement I had with Sauce Man in the beginning. I’ve only ever followed that feeling before—and look where it’s gotten me. When confronted with a communicative, emotionally available man who seems to really like me, I don’t know how I’m supposed to feel. Are those qualities more important than flirtation and fun? Are passion and peace of mind mutually exclusive? Am I reflexively rejecting the very thing I’ve been trying to manifest? Or is he just the first good example of what a quality partner can look like, a green flag that I’m on the right path? 

In trying so hard to break my old patterns, I feel like I can no longer trust how I feel. Is placid contentment how we’re supposed to feel in a “healthy” relationship? Or does passion still count for something, and I just need to learn to balance it out with substance and communication? How am I supposed to know if someone is a great match, or just a great person? I am truly confused, so I invite any of you in strong partnerships to reach out with your thoughts.

In the meantime, I suggested that he and I cut to the chase and discuss (over the phone or in person) what we’re looking for in love and life. While I don’t have a very good handle on how I should be feeling in love, I’ve at least gained recent clarity on where I’m headed in life—back to the west coast, in a year. If we can see whether or not our visions align, maybe that will help confirm what I am, or am not, feeling.


I’ll start by saying that Neighbor Boy and I haven’t had sex since before my last email. And we haven’t even kissed in the past 3 weeks. Why, you ask? Well, let’s take it back to when I was going to “crack open a can of worms.” That can of worms was referring to the 15-20 prescription bottles he had casually displayed on his nightstand the first time I slept over (date #3). I finally worked up the courage (maybe date #6 or #7?) to ask why there were so many in such a particular place, and he chalked it up to being messy and lazy. I obviously investigated and they were anti-depressants, so I naturally decoded that he has depression. About six weeks ago, he told me he was on a new cocktail of meds (officially revealing his depression to me even though his bottles were out and proud since the very beginning), and that it had completely killed his libido. This was fine though, and we were still having plenty of fun. But after a few weeks I realized we weren’t just not having sex, we also weren’t even kissing or cuddling, and it was hard to distinguish him from the rest of my friends, or to distinguish me from the rest of his friends. But he would still manage to pop up at the perfect moment and make it seem like everything was “normal.”

After a few weeks of confusion and uncertainty, I finally decided today that I needed to bring up that it felt like he didn’t seem interested and that we should just call it quits if he wanted. But then he texted me to grab a drink—and I knew he was on the same page. I met him after getting dinner with my friend, and we had a beer. As we were walking home, he initiated a conversation about how he wasn’t looking for a romantic/sexual relationship with me. We continued the conversation at his apartment briefly (read: I chugged the beer he poured for me as fast as possible), where I got him to admit that he couldn’t completely blame this all on the medication and that he did enjoy spending time with me, but he also doesn’t know how to separate his feelings from the medication and that he didn’t want me waiting around for the medication to figure itself out. It was very nice to be able to talk like adults, but I also felt tears threatening to show themselves in my eyes, so I left pretty abruptly. I knew the end was coming for a while, but that never stops it from being sad or disappointing. Since knowing each other, we haven’t run into each other at ALL in our neighborhood, and yet somehow I know that we’ll run into each other constantly now that we’re no longer hanging out. He better not show up at my pool this summer.

I do, however, have one lighthearted story to share. 2 weekends ago, I was at my favorite dance bar with my danciest friends. I told Neighbor Boy to come join us, but he was lame and didn’t show (red flag). Then, I just so happened to run into a guy that works on my floor and that I’ve had a mini crush on for years from afar. I struck up a conversation, and we ended up dancing, making out (sorry, Neighbor Boy), and swapping numbers. We texted a bit that weekend, and I haven’t run into him at work YET, but I know it will happen when I least expect it—probably on the same day that I run into Neighbor Boy in the subway. I initially felt bad about making out with a stranger after having committed to being exclusive with Neighbor Boy, but I no longer feel guilty now that he revealed that he hasn’t really given a shit about me for the past 6 weeks. What fun! At least I got some attention.

In other news, I’m finally getting an IUD next week. WHAT FOR, RIGHT???


I would first like to make it claro that Neighbor Boy and I did not celebrate Valentine’s Day. I had class after work and he was in Boston all week. He did reach out that day and we texted, but the day’s “holiday” was adamantly ignored by both of us. I’m assuming it was intentional on his part. It sure was on my end.

In other news, I’d say I’m less than satisfied with how much he’s been texting and/or reaching out as of late. Granted, he was gone all week, and then I’ve been gone for the weekend, but I also noticed that I had been the one to initiate most of our dates over the past couple weeks. So, I’m trying to pull back a bit, at least when it comes to advance planning. I can’t seem to gauge his interest, and figure this is a good step before deciding that maybe this is no longer healthy or fruitful. I know this whole situation has an expiration date, and maybe it’s looming sooner than I expected. He’s dealing with stuff, I’m dealing with stuff, we both agreed we weren’t seeking serious; but at the very least I need a guy to be interested in and excited to see me. Otherwise, there’s really no point. #shruglife


Well, hello again….lol

Neighbor Boy and I got ice cream, it was delicious, and we walked home. On the walk home, he worked up the courage to say that he’d been thinking about what I brought up on Sunday about exclusivity. (Remember that very brief chat I mentioned? It happened on Sunday.) And in my head, I just start laughing and thinking about how I actually just jinxed myself! But I’ll let him continue.

He said that he’s not seeing anyone else, and that he’s having a lot of fun with me, but that he’s also not in a place to be getting into a serious relationship, and that he doesn’t want to lead me on if that’s what I’m expecting. Phew. I was mostly just relieved he wasn’t reneging on our last conversation and telling me that he does indeed want to date other people. So I told him that we are pretty much on the same page, and that we should just keep each other updated on what we’re feeling and if other people are becoming involved and all that. Because in all honesty, I don’t think I’m seeking a serious relationship right now either. I don’t think I’m built to handle another real relationship that ends in real heartbreak (which I think is partially why the Universe has kept me from getting into any with the bozos you all know and hate). Besides—for various hippie reasons that I can discuss offline—I don’t think I’m meant to meet my person for a few years. And when we do meet, that will be that, and we’ll grow old and die together. So, at the very least, Neighbor Boy could be a great “practice” adult relationship, seeing as my only other experience happened mainly in dorm rooms.

The weirdest thing was that he then predicted me bringing up the fact that we probably don’t have to use condoms if we’re only hooking up with each other. That was spooky, but probably not totally out of left field on my part. Whatever, I’m new to this.

But for now, all is well, and we have plans to hang out on Thursday. Excited to see how it all shakes out! L.O.L.


I thought about not writing an update because I didn’t want to jinx anything, but I’m pretty sure I don’t believe in jinxes and I figure it’s good to have some hopeful positivity in here every once in a while. Suffice it to say that Neighbor Boy is still in the photograph.

We’ve hung out 10.5 times, and we recently, very briefly talked about how we are not currently seeing anyone else. I didn’t think he was, but I felt the urge to ask. I’m trying to trust my gut and give it what it needs, like less dairy and more uncomfortable conversations.

Notable happenings:

  • On one occasion, he got a bloody nose ON my face, and it was pretty hilarious. It looked like I got punched and I really wish I had taken a photo. It was also the perfect opportunity to ask if he has any bloodborne diseases I should know about. Sneaky me! (He doesn’t.)

  • We watched his friend’s dog one evening, and it was in the room (my whole apartment is one room, after all) while we did stuff. My first voyeur! That I know of… (Actually, the dog was pretty respectful and/or didn’t seem very interested.)

  • We ate donuts in a park and witnessed a HAWK snatch up a critter for breakfast.

  • We are getting ice cream tonight. *~future happening~*

  • I apologize for starting with the best happening and having it get kinda boring from there. Shrug. Byeeee!


Neighbor Boy pleasantly surprised me by texting quite a bit while I was gone. He didn’t forget about me! In fact, he invited me to his friend’s NYE party. I loathe New Year’s, but figured I should go if I could be guaranteed a kiss, and then some. The party was about 20 people, and everyone was very nice and cool. In the Lyft home, Neighbor Boy said I was “heroic” for going to a party where I knew nobody and getting along just fine. Having once been told basically the opposite by my first ex, I was pleased to hear that I’ve improved my party skills. (Thanks, alcohol!) I also reminded him that he did the same exact thing at my holiday party.

We stayed in bed until 1 on 1/1 because I was nauseated from all that beer and champagne. I even had to poop a little at his apartment, but I think that’s better than vomiting, no? Before I left, he asked if I wanted to eat pizza and watch a movie later. I said yes, and went home for a few hours to wash up, do laundry, and nurse my hangover.

The fact that we are neighbors makes seeing each other ridiculously convenient, and I totally get why older generations married whomever lived down the block. It’s definitely fun, but I also feel like we’re hanging out in the shallow end of each other, and we could absolutely get to know each other better. I already have some burning questions, and am mentally preparing myself for the can of worms I will surely crack open!

*Unfortunately for this update number, there was no 69, but there was a 6 and there was a 9.*


Neighbor Boy came to my holiday party last Friday. I told him to get there an hour after it started because I was nervous that he might not be fun or it might be too awkward, and I needed a drink to prep. But he turned out to be a delightful date, and everyone loved him. He was outgoing and self-sufficient when I had to abandon him to go pee. I was relieved. We ended up going to his place, but didn’t get past making out because he has a Casper [this is not a sponsored post, unfortunately] and we were wasted and I fell asleep very quickly. I spent the night and there was lots of cuddling. Then on Monday, we got drinks and eventually picked up where we left off before I had passed out on the previous occasion.

After all this fun, but then not hearing from him for a couple of days, I looked back and realized I had initiated most of our texting as well as our last 3 dates. It got me wondering if he actually likes me or if I’ve just been presenting very convenient and fun opportunities for him to take part in. In the spirit of testing his interest and laziness, I’m taking a step back from reaching out. He did end up texting me last night and we’ve talked a bit since, but I fly home for 9 days tomorrow and we all know how helpful that is for a budding relationship. We’ll see what happens, but I’m gonna play it cool and try to only initiate letting him know when I’m back—which I guess means hiding my phone from myself while I’m high all week? All in all, all is well. After all, I AM THE PRIZE!



On Tuesday, I got a couple drinks with a nice guy who lives around the corner from me. I really started to loosen up and relax when we started talking about student loans and credit card rewards. #romance

On Wednesday, I had a laughably bad date with a real douchebag. I definitely saw it coming and was mentally prepared for it to suck, but he still managed to shock me. We first started talking before Thanksgiving on Bumble (which I can’t say anything positive about lately; it’s just a wasteland of lazy assholes) and he was quick to let me know that he was just looking for something casual/sexual. I thanked him for being so upfront and we swapped numbers. He was decidedly not chatty and would abruptly end any text conversation I tried to make happen. I stopped trying, and we eventually met up. His first suggestion was that we meet at his apartment, but I told him I definitely didn’t want to do that. So we met at a super loud and fratty bar in the city by his apartment (thankfully, I was already in the city that evening). I got there first and bought my beer with cash. He then showed up and ordered a “vodka soda with lime.” We sat at the bar and he somehow managed to face fully away from me, spending most of his time looking at himself in the mirror behind us. The conversation sort of felt like an interview, but I tried to make the best of it. He was cute in an obvious way, with a super tight shirt and hilariously tall hair. He was drinking his drink pretty fast, so I followed suit. At the end of our drink, he asked if I wanted to get another drink at his place or another one at the bar. I said I didn’t want to go to his place but could stay for another drink at the bar. He paused and then responded with “Actually, I’m not going to get one.” I was really dumbfounded for about 4 seconds. And then I realized what was going on. So I grabbed my stuff, automatically said that it was nice to meet him, and left him there trying to get the bill for his drink. I got onto the street and audibly said to myself, “So why even offer that as an option???” Apparently, because I had been “open” to something casual/sexual, he thought I had been a sure thing without needing to tolerate his personality. So. Fucking. Gross. Worse than the Trump supporter, tbh. But at least it only lasted 45 minutes.

On Saturday, I had a snowy day date with Neighbor Boy. In previous texts, he had joked about living on the edge, so I had asked if he wanted to go ice skating with me (ya know, cuz you’re literally on an edge), and he actually agreed! We met up around noon to get coffee, and then ambled to the park in the snow. We skated for a while and then ambled on back. (The park was a goddamn winter wonderland, it was so cool.) He’s super fun to talk to and there weren’t really any awkward moments in the 4.5 hours we were together. We kissed at the end of the date, but our faces were covered in snow and snot, so it was kind of disgusting. We’re still texting and I invited him to come to some part of my company’s holiday party this Friday. (COWORKERS, GET READY!!!! But also be nice and not weird, please. Initial judgements welcome, though.) I figure it will be a good way of throwing him in the deep end, so to speak, and seeing if he’ll sink or swim. Plus, I feel like we need to make up for being so sober on Saturday.