#103 Emily 2.0 is Live

PART 3

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.

#102 Emily 2.0 is Installing…

PART 2

I think it goes without saying that I’m a power user of dating apps. Having come of age on AIM (the locus of the entirety of my 7th grade “relationship”), dating apps allowed me to flex the only flirting skill I ever developed: strategically deploying witty banter from behind the eye-contact-free safety of a screen. 

I admit it: dating apps were absolutely a crutch for me. Sure, crutches slow you down and hurt your armpits, but they also help you walk when you can’t do so on your own. A naive 22-year old new to New York City, I wasn’t a fan of talking to strangers and I didn’t understand how adults made friends, let alone lovers, outside of work. (Plus, I worked at a company where dating coworkers was “not allowed.” FML for being such a rule follower, but also clearly nobody was interested, lol.) I was also poor, and apps made it so I didn’t have to spend money at a bar in order to maybe talk to guys. I could sit on my couch for free and take my time crafting the perfect response. Bless the innovation! 

And helloooooo, this entire newsletter is a testament to the fact that the apps fucking work! Perhaps too well. I never really gave myself a chance to meet people IRL because I could always play it safe and shy by relying on the apps. There would always be another batch of men who might love me, if I just kept swiping. In fact, I’d inevitably get FOMO any time I was off the apps for too long. What if my person was just a few more swipes away?! 

This is the dark side of the apps, the reason (I suspect) most people don’t chat up strangers in the wild like they used to. Endlessly defeated by the fact that guys would rather hide in their phones than bravely approach such a magnificent creature (me), it finally struck me that I’ve been a hypocrite doing THE EXACT SAME THING. 

Although it wouldn’t have mattered if they did approach me. Scared to let anyone in, I would have shared just enough to gain the information needed to morph myself into someone I’d assume they’d like more. I would tell myself they didn’t “deserve” to know the real me yet, when really it was just my way of protecting myself from judgement/rejection. Clearly a winning strategy! 

So here I am, once again, claiming to be “off the apps for good.” I don’t blame you if you don’t believe me; I’m well aware I’m the Girl Who Cried IRL. But lately, in addition to being consistently frustrated by the seeming lack of quality options on Hinge (I gave up on Bumble and Tinder loooong ago), I’ve also been feeling limited by my own profile. Having recently arrived in a place where I feel comfortable showcasing my true self—no matter how polarizing she might be—I discovered how difficult it is to convey my Many Incredible Facets in just 6 photos and 3 prompts. [Not to mention the fact that concisely-and-creatively-communicating-a-variety-of-value-props is literally what I do for a living! So if it’s hard for me, I can only assume it’s even harder for these guys—which is probably why their profiles are all so trite and tiresome.] I started to notice the pessimism that bubbled up every time I opened Hinge, and it felt like a self-fulfilling prophecy—the digital equivalent of sitting at a bar with crossed arms, a sour face, and expecting anyone to approach while expecting, and exuding, the worst.

Officially fed up with the limitations of this stable source of in-cum, I guess you could say I’m going romantically freelance? In the same way I’ve learned to clearly articulate the type of work I’m looking for in my independent career, and confidently say “no” to projects that don’t meet those standards, I look forward to navigating the social seas with:

  • The confidence to ~*bE mYseLF*~ and wave my freak flag proudly,
  • The optimism that my particular brand of freak will tickle the fancy of at least someone, and
  • The courage to prioritize my values and boundaries over the inane desire to be liked by everyone.
  • (Also, some smiles and more approachable body language probably can’t hurt.)

However, I owe much of my professional success to word-of-mouth referrals, so I trust you’ll do your part in singing my praises (personality, beauty, humility, etc.) whenever the opportunity presents itself.

P.S. I forgot to mention that, a few days before I wrote Part 1, I was at an outdoor yoga class when, who puts down their mat directly in front of me? Sauce Man’s cousin. I said hi and we chatted for a bit before class started—it was actually nice! Turns out she recently moved just a few blocks away from me, so I’m sure we’ll be bumping into each other more frequently, LOL. Neither of us brought up Sauce Man, which is great because I genuinely want nothing to do with him the more I reflect on what I can now see was a very unhealthy relationship. Ya live and ya learn.

P.P.S I hope you’re not sick of my painfully-late-in-life revelations just yet, because you better believe there’s going to be a Part 3.

#100 Happy 5 Years …to this eccentric email experiment

No word from Sauce Man, as expected, but I did run into his Hinge profile last weekend. His answer that initiated our matching (”Typical Sunday”) changed from “running, edible, errands” to “long run, spliff, errands.” He also updated the cigarette section from “Never” to “Sometimes.” I don’t know why he’s intentionally making himself less attractive to potential mates, but maybe my complete intolerance of his slowly-increasing tobacco use really bummed him out. He’s also now seeking an avid runner (I guess I wasn’t athletic/outdoorsy enough in the highly specific ways he wanted), so I wish him the best of luck in finding a health-oriented woman who is cool with cigarettes. There’s someone for everyone!

On a similarly adjacent note, I was in a rooftop yoga class Thursday morning when I spied Sauce Man’s cousin a few rows back. She doesn’t live nearby so this was especially random. I intended to say hi to her after class because 1) I did like her, and 2) I wanted to prove I am gracious as fuck and doing really well—but as the Universe would have it, it started to rain and I had to bike home before it got worse. In the end, I think it was probably for the best that we didn’t interact.

But anyways, back to Hinge. A few weeks ago, my friend shared a guy’s profile with me, so I had no choice but to recreate my own to engage. Since then, a few guys have asked me out on IRL dates, but our conversations weren’t riveting or even complete enough for me to risk meeting up during a pandemic only to have our first interaction impeded by masked facial expressions. Plus, having missed out on the virtual dating boom of early quarantine, I had been looking forward to meeting men in the safest, laziest way possible.

The one guy who asked me out for virtual drinks seemed pretty cool, so I agreed to MY FIRST ZOOM DATE. Last Wednesday night, I made myself a martini and we chatted for almost 3 hours. It was awkward at moments, but enjoyable overall (so, like, the same as most offline dates?). I have no idea if we’ll have a second virtual date or *gasp* an in-person date, but the gentle ego boost from our sustained, sporadic texting is all I’m really looking for as I continue to focus the majority of my attention on ME ME MEEEEEEEE!

#99

As some of you may know, Sauce Man and I broke up the day after Memorial Day, a week and a half before our 6-month anniversary. 

The first 4 months of our relationship were a whirlwind of fun, joy, and romance. It was great to be my weirdest self with someone again, and it was just plain nice to both have and be a someone. It really felt like we’d known each other for years. Maybe that’s why we assumed we knew each other better than we actually did. It truly felt like we were falling in love, but ultimately we were stopped short. 

Mid-March, I told him I loved him. He told me he “hadn’t really thought about it.” I think that’s probably when I started shutting myself off from him, little by little. Withholding my vulnerable, truest self until he “deserved” it by saying it back. Not a winning strategy, to say the least.

Then quarantine happened and the momentum we had gained suddenly turned us into an old married couple, but in a bad way. Only allowed to see each other, we started spending all of our free time together, and I think I lost myself a bit. Desperate for him to feel what I was feeling, I let my world revolve around his, and made more time for him than for myself. 

Mid-April is when we had our first big talk. (If I’m being honest with myself, that’s when I knew deep down that we were doomed.) I don’t think either of us knew if quarantine was to blame for the changes in our relationship, but we decided to roll things back a bit in order to recapture our spark—which sounds completely illogical in hindsight. Instead of connecting more and going deeper, I was made to hold myself back from my supposed “boyfriend.” Red flag.

And things did get better, for a time. We celebrated his birthday (no more Tauruses, please!), we Zoomed with his friends, we hiked and biked. But we still weren’t communicating. We weren’t being intimate in any sense of the word. And I went along with it. I saw all of the red flags, and I didn’t speak up. I ignored my gut and pretended everything was fine. I lied—to him and to myself. 

So when we had our second big talk in mid-May, I was ready. I knew things hadn’t been good, and I knew it was because we weren’t talking about anything real. A lotttttt of stuff came out during that conversation. Like how apparently there were a lot of small things I did that bothered him—like talking too loud or not managing my time well enough. And instead of bringing them to my attention and talking about them, he tried to manage situations so that I wouldn’t “do” something I didn’t even know I was doing to annoy him. That felt fucking patronizing. Plus, bigger differences—like how we approach money—were becoming obvious as well.

At the end of that conversation (which actually ended on a positive note), we decided to not talk for a few days, so that we wouldn’t immediately resort to our old patterns—like we did after our first talk. He was going to his cabin for Memorial Day weekend (alone—because instead of thinking a change of scenery and a weekend away together could be beneficial, he assumed we’d have a bad time together………………..), and we’d regroup when he got back. That’s when I finally started asking myself what I really wanted, and if I actually wanted to be with him, now that I knew more about his views and values. After a much-needed “me” weekend of journaling and vision boarding (and honestly not missing him all that much), I concluded that while I didn’t yet know if we were a perfect match, what we had together was special enough to keep trying.

On May 26th, he came over at our prearranged time and we talked. Well, mostly he struggled to convey his thoughts and reflections. After a somewhat confusing monologue, I finally had to ask him if he wanted to keep working on us or if he wanted to end things. He wanted to end things. I guess as much as a guy “respects” you, thinks “you’re a badass,” and claims you’re “probably the best girl he’s ever dated,” none of it matters if he’s not willing to fight for you. 

Before leaving, he asked if we could hug goodbye. I reflexively said “no” but then acquiesced. I told him I’d miss him, he said he would too, and then he took the longest time to exit my apartment: fumbling with the door knob he’s opened a million times, and staring at me with what I can only assume was remorse as he closed the door on himself as slowly as possible. It was a scene right out of a tragic love story, and I just wanted it to end. 

The next day was the worst day I’ve had in a really long time. I slept in, blew off work, and cried a lot. Everything hurt and I hated every minute I had to feel it. The day after that, I already felt so much better. Still a bit down, I was mostly back to normal after 2 or 3 days. I actually started to worry about how “well” I was handling it. And while I’ve had a few bad days since—most of which have been due to the guilt and responsibility I feel being a white person in this repugnant society—I know I’m better off.

While I’ll never know if quarantine was the “reason” we broke up, I like to think it fast-forwarded us to an inevitable realization that might otherwise have taken us way too long to grasp. And for that efficiency, I’m grateful. 

I had some amazing times with Sauce Man, but I also learned a lot—about relationships, myself, and what I really want. Sauce Man might have been my boyfriend, but he was never my partner. And that’s what I’m looking for now. 

My 20s have been a rollercoaster of sex and love, heartbreak and hilarity, lessons upon lessons, and an uncomfortable amount of self-reflection. As I prepare for my 30s, I’m finally getting clear on what I want, and I refuse to settle for anything less than what I deserve.

To Sauce Man and all the characters who came before him: Thank you, next.

#98

Remember Degrassi Dude? Apparently he moved to Park Slope, because I had my walker shift at the Food Coop last month and HAD TO WALK HIM AND HIS GROCERIES TO HIS APARTMENT. I didn’t recognize him until I was too close to hide/make him wait for another walker, but I greeted him with a “Hey!” that I assumed communicated, “I recognize you, but let’s not make this weird.” However, I’m not sure if he recognized me (??? Is this even possible? I guess I was wearing a hat…) because he tried to make small talk, which I quickly shut down with a “Fine” and proceeded to walk 3 steps behind him for our mandated 10-minute stroll. It was from that vantage point that I noticed his bald spot had increased :-/

Entirely unrelated, I have since switched my coop shift to another team, day, and time :)

Otherwise, I’m still dating Sauce Man!

#97 Caught a cold, and a boyfriend

Surprise!

I met him 1 month ago, but it feels like we’ve known each other longer. After matching on Hinge, we squeezed 5 dates into 12 days before I left for the holidays.

Timeline

Date 1: Started with beers, ended with ramen.

Date 2 (24 hours): Edibles at the NY Transit Museum, brunch at a diner, beers at a dive bar, spontaneous decision to join him at his friend’s party (where I made all his friends love me), pizza & sleepover at my place. (This is when he gave me the cold)

Date 3: He cooked me dinner at my apartment AND washed the dishes. That’s when I knew I’d found myself a Sauce Man.

Date 4: He came to my friend’s holiday brunch, where he met and impressed a few of my pals. He told me he deleted the apps, and I accidentally called myself his girlfriend (facepalm).

Date 5: Dinner and a movie.

*[I went home for the holidays for nearly 2 weeks, but we texted and video chatted plenty]*

Date 6-?: 48 hours with all of his friends (who I actually like just as much as him) at his family’s cabin for NYE. ‘Twas a grand ol’ time.

This past weekend, we/I decided that a normal enough amount of time had passed to call this what it is.

Details

Name: Sauce Man

Age: 3.5 years older than me

Occupation: former physics teacher, works in education

Hometown: upstate NY

Hobbies: cooking, running, being really nice to me

I’ve been single for nearly 7 years, so I’m a little rusty when it comes to sharing myself with another human—but so far, so good. However, we’ll see what happens when I inevitably tell him about all of THIS…