As soon as I was invited to my friend’s New Year’s Eve wedding in Miami, I was on a mission to kiss an(y) eligible bachelor at midnight and, ideally, get laid. 

The plan was simple:

  1. Beg the happy couple to seat me at a table with single men
  2. Pack condoms
  3. Look hot & win everyone over with my undeniable charm

Dec 31 – The Wedding

The ceremony was insanely beautiful, I cried, blah blah blah. However, as we located our seats for dinner, I felt betrayed when I discovered I’d been seated at a table with exactly zero single men. My one request had been brutally rebuffed. Nevertheless, I persisted. 

I ended up identifying two contenders:

  1. Another single gal’s platonic plus-one
  2. A friend of the bride I once met a few years ago

I danced and chatted with both, but felt more of a vibe blossom with the second. When dessert was announced, I forced my wingmen (my good friend + her husband) to accompany me in relocating to his table, where he and I talked for a while.

Fast forward to midnight: champagne was passed out and we all clinked and cheered on the dance floor. Despite being paired up in a crowd of actual-pairs, he and I didn’t immediately kiss. After 30-60 seconds of awkwardly bobbing amongst the couples, I told him, “we can kiss if you want.” He laughed and so we did. A little bit later, he asked me if I had explored the rest of the massive tropical backyard extending beyond the party. I’m no dummy, so I joined him for a stroll—i.e., we made out on the dark garden path. As the wedding wound down, he asked for my number and we talked about meeting up in Miami Beach the next day. 

Jan 1 – The Next Day

After having lunch with my friend, I met up with him and his friends at the beach a little before 4pm. About 30 mins after I arrived, his friends decided to head back to their Airbnb in downtown Miami to shower and change before dinner. He hung back with me and we stayed on the beach for another half hour, until it got too cold. We walked the few blocks back to my swanky hotel so he could use the bathroom before calling a car. We chastely kissed to break the tension. His friends were still stuck in traffic and Uber was taking forever; his car wouldn’t arrive for 30 mins, so I told him he could shower. I showered after him, got dressed, and we proceeded to make out because what else were we supposed to do? After a while, he got a notification that his car had been CANCELED. Thank you, Universe! So, he told his friends not to wait up for him and we spent the next couple of hours having a very good time. Afterwards, we grabbed dinner nearby, he finally got a car home, and I snuggled myself into bed, exhausted and extremely proud that my cute ass hotel room did not go to waste. 

:) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :) :)

After breaking my TWENTY-month celibacy streak, I was flying high. I had achieved my goal, ringing in the new year with hotel sex. I wasn’t even that upset when our 2-text conversation the following afternoon led to half-a-week of total silence. Confused, yes. Heartbroken, no. 

When my therapist (Emily 2.0 goes to therapy!) pointed out that I seem to worry more about what other people want instead of focusing on what I want, I paused to reflect on what I actually wanted from Goodtime Guy. We have mutual friends and had a lot of fun together; so, naturally, I wanted to explore if there was something there. I decided to ask him out. (Go, me!) He asked if that was my way of inviting him back to my bed (my response: yes and no), and then gifted me the following:

“Real talk tho, what we had in Miami was very fun and I’d certainly love to find that sweet spot again, but you should know I’m not looking for anything serious and don’t want to lead you on if you are.”

God bless a man who hates ambiguity. With the possibility of a relationship no longer on the table, I was freed to solely consider whether or not I want to continue having mutually enjoyable sex with not-a-sociopath, without constantly speculating if I’m doing “it” “right” to “ensure” he falls in love with me. My heart, mind, and clit joined in a resounding chorus of “YES!” So, I thanked him for setting expectations, and granted him permission to booty call me.

Now, in case you’re worried that I’m deluded or energetically blocking myself from finding My Person, allow me to share this relevant digression about how my successfully-casual relationship with The Comedian came to be. For our second “date,” he invited me to his apartment while his roommate was gone. We got naked pretty quickly, and had a grand ol’ time. When we texted a few days later, he told me he wasn’t looking for anything serious, but would want to hook up again. I took a minute to remind myself that he was far from “boyfriend material,” and thus responded in kind, telling him I wasn’t looking for anything serious with him either. Presented with a nearly identical situation 7 years later, I have no qualms about leaving the door open for more play, pleasure, flirtation, and fun. 

Don’t get it twisted: I’m still eager to enter partner mode, but I’ve decided to slow my roll and try to go about it with a little less severity. Over the past year, I’ve been unable to meet a man without immediately analyzing whether or not he could be The One. In fact, I’d be lying if I said I wasn’t doing exactly that at the wedding. I can only assume it’s imbued me with a desperate intensity that inadvertently repels anyone who piques my interest. 

For the sake of not ruining my own surprise of who I end up with, I surrender. My new strategy (my therapist also pointed out that my need to “strategize” finding love could be something to explore…) is to have more FUN and create a life I actively enjoy. I had an excellent weekend in Miami; not because a guy slept with me, but because I did exactly what I wanted. I listened to my sacral chakra—and even got someone to touch it. ;) And I want more of that! More flirting, more dancing, more makeouts, more leisurely rolls in the hay. More sexual encounters where I ask for what I want and am greeted with enthusiastic teamwork. By following my bliss wherever it leads me, I can only assume I’ll become even more irresistibly magnetic and attract the very best person for me. If not, at least I’ll have a good time along the way.

#103 Emily 2.0 is Live


It’s been 14 months since my mouth was caressed by that of another, let alone my genitalia. For me, the lack of kissing is more concerning than the lack of coitus. I’ve been making out far longer, and more frequently, than I’ve been knocking boots. 

When I first had sex at the ripe old age of 21, I was so excited to be fucking AT ALL (and relieved I wouldn’t be graduating college a virgin), that I didn’t even consider the possibility that it could be better. All I knew was that it felt good and we were falling in love—what more could I have asked for?? Apparently, a lot! Which would only gradually dawn on me over the next near-decade of mostly-mediocre sexual encounters.

The main issue with my subsequent lovers was that we never dated for longer than a month or two (Diet Coke Dealer somehow made it to the 4-month milestone). Usually, by the time I identified and slowly worked up the courage to suggest something different, I’d already been ghosted. So, when I was finally in a relationship with Sauce Man, I didn’t know how to communicate what I wanted from another person, because nobody had ever hung around long enough for me to figure it out.

Telling myself I had no idea what I was doing, I allowed most of my sexcapades to be driven by the guy. And with the exxxception of The Comedian, most of those interactions left me far from the finish line. It wasn’t until Diet Coke Dealer told me that he “could literally have sex with a hole in a wall and still finish” that I finally started to consider answering the dreaded-and-therefore-deflected question: “What do you like?” 


With minimal WAP-worthy memories to long for, a sexless year in quarantine was no death sentence. After all, masturbation was always a sure thing. But how often was I even doing that? A few years ago, an energy healer told me that my sacral chakra was “barely ticking” (a healthy chakra should be happily spinning), so she gave me the assignment to have 4 “releases” per week. Let’s just say I rarely completed my homework. 

Then, inspired by the habit-building efficacy of the 60-day Sanctuary Challenge, I decided to take my self-care up a notch with a self-imposed 60-day Orgasm Challenge. I found a friend to be my accountability buddy, and we spent March and April texting each other about our commitment to a daily orgasm. 

I naively assumed that by Day 60, I’d be positively radiant with the flush of daily pleasure. But the challenge turned out to be a lot more challenging than I expected, and I only “achieved” orgasm 33/60 days. (What began as a daily commitment to prioritize self-love, soon became just another opportunity to flex my toxic perfectionism.) At first, this felt like a failure—until I realized the real challenge was getting clear about what I want when it comes to sex and intimacy.

On the 27 days when I couldn’t check the box (could be a new euphemism, but I really was keeping a written tally), I was either too tired, too stressed, or simply not in the mood. Once, I texted my friend: “I hate how busy my work is right now. I’m not a great lover when I am overworked.” Sadly, this was a revelation for me.

Another time, I told her: “I ended up missing yesterday and chose not to force one before bed because I’ve been doing that a lot and it doesn’t feel 100% consensual haha.” This made me shamefully realize how accustomed I was to “forcing it” with partners. Reticent to reveal my desires—or anything beyond the vulnerability required to allow another person’s appendage inside my body—I had always assumed it was my job to rev myself up if they couldn’t be bothered to magically read my mind. 

There were even 2 days where I truly tried my best to take myself to O-Town, but just couldn’t get there. After one of these, I texted her: “So I tried last night but didn’t finish. It’s like I also need to commit to seducing myself.” Yet another tragic breakthrough. In the same way I dry up at being commanded to “CUM 4 ME,” I realized how hard it is for me to get off under any kind of pressure—regardless of who it comes from. (Don’t even get me started on quickies.)

In the end, my 60-Day Orgasm Challenge (powered by Unbound, Dipsea, and NSFW XConfessions) turned out to be about a lot more than just orgasms. Sexy stuff aside, it helped me appreciate how much energy a romantic relationship requires—even when it’s just with yourself. Until (but also after) My Partner arrives, that’s the relationship I’ll be focusing on.

Now, whenever my ego is temporarily bruised after a night out cruising for guys with my annoyingly-hot friend, I can always console myself with the reminder that, 1) it’s fine that he asked for her number over mine because I don’t date boys who still have roommates, and 2) I’m hot, too, so I might as well go fuck myself.



This is what’s happened in the past month and a half:

  • I went on a date with a long-haired British boy. He was nice and cool, but I don’t think either of us are upset that he never texted.
  • About a month ago, I slept over at The Comedian’s for the first time, because we were drunk (also a first, actually)—so that’s back.
  • I got drinks with an overly aggressive and therefore creepy guy who I’m glad I never have to see again. All I can think when I recall that date is “blech.” (I might be making it sound worse than it was.)
  • I went out with a very nice boy last week who brought a coloring book to the date! #DTC (I brought the colored pencils.) Then we got drunk and made out. We’re getting ice cream tonight.
  • I saw The Comedian again on Saturday night, and he referred to it as a date which is kind of confusing me. We went out for drinks (we don’t normally do this), and then he slept over at my place (also not normal). I don’t fully understand why we’re suddenly going out and sleeping over, but whatever. We are definitely not dating—I know that.
  • I have a first date on Thursday and potentially one on Sunday and I’m excited about neither!
  • I’m still majorly crushing on the forbidden not-my-actual-client, and we now live 2 blocks away from each other, but he is moving to SF soon… so, yea. I can’t tell if he’s super nice and weirdly touchy with EVERYONE, or if he likes me—but I’ll assume the former.
  • My latest dream is to meet a beautiful earth-friendly man at the Park Slope Food Coop, of which I’m now a member. That, or finally convincing fellow owner/worker/shopper Jake Gyllenhaal that we are meant to be.


As a newly matured, 25-year-old woman, these are my updates:

  1. I’m going to Party Gent’s parents’ house for Thanksgiving. Before you FREAKTHEFUCKOUT, it’s just as friends AND two other guy friends are going, too. However, he did offer me birthday sex, so I’m pretty happy I was out of town—and I hope he never brings it up again.
  2. I saw The Comedian for the first time in quite some time last week. So that’s another reason/reminder why I don’t want to sleep with the less-than-spectacular Party Gent again.
  3. Baseball Boy says he’ll be in town the first week of December. Third date??? Mixed feelings because now he becomes real again. And I still don’t know when exactly he’s moving back for good.
  4. In general, I’m feeling pretty burnt out by all these gosh dang dating apps (as I assume most of my peers are), soooo there’s that. Still truckin’ though!


Still hanging out with Party Gent, but still feeling the same mediocre feelings. We probably hang out about once a week. There are many qualities about him that do not thrill me, but the overall experience is pleasant. I’m a little unsure of what I should do… I am 90% sure this isn’t going anywhere and won’t go anywhere due to my reservations, but does that mean I should cut it off right now? Part of me feels bad “leading him on,” though I can’t even be sure that’s what I’m doing because I really don’t know how he feels. He could care less for all I know. (He could also be in love with me for all I know, I guess.) The other part of me says, “Have fun! Who cares?” Another part of me wonders if I’m “wasting my time,” but I’m also not trying to get married tomorrow, so I dunno? Everything feels very hazy, but I’m assuming things will come into focus and/or end when things start to feel more serious than a weekly hang. Maybe he’ll suggest we “talk”? Whoooo knooooows. I do have to say, though, that the sex was better with The Comedian. Oh well, better than nothing! :-/

And, obviously, Balloon Boy was a one-hit-wonder.


It was a new year, and I had resolutions. Except that when I saw the cute boy at my coworker’s birthday party, I remained sober and silent. So the next week I told the birthday girl to pass along my info to said boy. She did, and that was that. Nuthin.

Then I met a vegetarian from Hinge who went to college with some high school friends of mine. I met all of his friends on the second date, slept over (nuthin), and spent the following day watching the entire season of Transparent with him and his friends—ALL DAY. Then it fizzled pretty quick when he said he wanted to be friends—fine. Remember, vegetarian. This was all within 2 weeks.

In February (after V-day of course), I met Paul (I don’t really have a nickname for him…). He works in Dumbo too, so we met for a morning coffee before work. He texted me A LOT. Which is great, unless that’s all you do. We went on one more date where we ate poutine and pickles; it ended in a donut, but no kiss. It continued/fizzled strictly via text from then on. I’ve already awkwardly-seen-and-tried-to-avoid him twice in the subway going to and from work. Thanks, Happn.

March passed by pretty uneventfully, despite meeting two single NYC banker boys while in Vegas.

In April, I met a funny boy through Hinge who turned out to be a comedian. We have since been casually and very sporadically popping in and out of each other’s beds. (Please note: aside from this, I think Hinge is completely worthless.)

The week I came back from Argentina in June, I went out with a Jewish Doctor Who Has a French Bulldog. We had matched on Tinder last fall; I had given him my number and he never texted. Long story short: we met a week or two after he moved to NYC for residency. I had four drinks, including a suggested tequila shot… which means I was wasted. We briefly made out on a street corner but he was, in my opinion, too muscley for his stature and I wasn’t that into it. Very nice guy and great to talk to, though. We texted once or twice but never made plans to hang out again.

This was partially due to the fact that right before meeting Jewish Doctor, I had matched on Bumble with THE BOY FROM THE BIRTHDAY PARTY. I messaged him, he took two days to respond, and then we got into a nice, but brief conversation. I was eager and asked him out. He exclaimed and agreed! Our 3.5 hour/3 drink date was objectively amazing for both parties. Unfortunately, it was all downhill from there, despite having a second 5-hour date—2 of which were spent on his couch talking, and ONLY talking. He tried to quit it with the “ack my schedule got crazy, I can’t meet.” But when I boldly checked in about hanging a week later, he went with The Classic: silence and pretending to not exist. I sure hope we don’t run into each other at a party thrown by my coworker again… :) And, obviously, I never asked why he never put my number to use way back when.

Just last week, I went on a date with another guy from Bumble. We didn’t talk much upfront but he seemed cool and direct. We went to an awesome speakeasy and he was great! Very fun to talk to and it seemed we had a lot in common (mostly baseball). No kiss, but we agreed to do it again sometime. THEN, I decided to stalk him on Instagram… where I discovered that just 10 weeks prior (and possibly even more recently) he had a girlfriend of 2ish years. I obviously don’t know what the situation is, but now I’m healthily wary. We discussed hanging out this past Wednesday but he had to cancel due to work and preparing for a trip—he asked for a “rain check” (classic baseball move). TBD, but I’m not expecting to hear from him ever again, a la boyfromthebirthdayparty.

There have been a couple other dates in the past couple weeks (even one last night), but they were nothing to write home about—so I won’t.

Also, there may be a charcuterie date in my future. To be continued.

This inaugural entry should be the longest you’ll ever have to read.

Thank you,

and Welcome to…

The Amusement, Bemusement, & Crap of Dating

by Emily F!@#in’ G.