#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.

#101 Emily 2.0 is Loading…

Hi there. Remember me? It’s fine if you don’t, because I actually think I might be an entirely new person.

PART 1

After a paltry pandemic picnic date last September, I decided to put my love life on pause because covid dates—bereft of any potential for physical contact—felt more like job interviews than romantic encounters. Then, at the end of November, I decided to start the book Calling in The One. Despite its cringe-worthy cover, it’s actually incredible, akin to 7 weeks of free therapy. I learned A LOT about myself and why I’ve been emotionally unavailable for the past 8 years, realizing that a lot of it* stemmed from my upbringing. (Soooo nice to be able to blame my family!) Jokes aside, I uncovered and began undoing a lot of internalized beliefs, suppressed memories, and other fun demons. 

*Not to mention the fact that 8 years ago is when I swept up the shattered pieces of my heart and unconsciously sealed them away so as to avoid ever again experiencing the blinding pain of being gently dumped by my first love, not because he stopped loving me, but because we were genuinely in two very different places in our lives and it simply wasn’t going to work out. But that’s a tragic tale for another time.

Supplementing Calling in The One with The Sanctuary Challenge and The Artist’s Way, I’ve come out the other side committed to: 

  1. Always sharing my authentic self, thoughts, and feelings (Because how can I expect anyone to love me if they don’t actually know me?)
  2. Establishing and protecting healthy boundaries (with work, friends, family, and beyond)
  3. Showing myself the love and care I want to receive from others (Stay tuned to learn about my self-imposed 60-day Orgasm Challenge!)
  4. Consistently expressing my love and appreciation for others (This one is fun, because the more you do it, the more it comes back to you from all directions)

It’s taken a whiiiile, but I finally feel truly OTL (aka “open to love”).

However! I acknowledged that all my newfound revelations and commitments to change would remain purely theoretical unless I put them into practice, so I slowly got back into dating this year. I used Hinge to go on a handful of Zoom & IRL first dates that were objectively enjoyable, but none of us ever followed up. After this happened a few times, I began to consider the possibility that these men were merely practice tests that I was clearly passing, and the Universe didn’t want me wasting any extra time or energy on them.

But in the middle of this First Date Only epoch, I went out with someone who seemed so freakishly perfect for me, that I became 95% certain I manifested him. I could literally point him out on my vision boards (lol). We only went on two dates, but a host of synchronicities plus some very strong intuition pings convinced me that, after less than one week, this was my husband. 

Initially, out of habit, I told myself “not to get my hopes up.” But aren’t hopes energy? Aren’t they the “positive vibes” we squirt out into the Universe when we’re trying to manifest something? If this is true, then I’d be a FOOL not to send those hopes as high and far out as possible for something I really want. So, I fucking let myself fall down the rabbithole of believing I was finally getting everything I’d been asking for. It felt wild, thrilling, ridiculous, and liberating. I assumed I was feeling all the things one feels when recognizing their Person. 

Long story short, he didn’t turn out to be my husband. I told him I’d like a 3rd date, and he told me he “didn’t think we were the most compatible.” But miraculously, I did not die! I’d been vulnerable, I got rejected, and yet my kintsugi heart remained resilient and whole. I wasn’t even that upset. Mostly, I was confused, feeling led astray by my extra-strength Scorpio intuition. But maybe I had simply read those intense gut feelings incorrectly. Maybe he’d been a new type of test; one that challenged me to shoot my shot when presented with someone too good to miss out on. If so, I appreciate the practice.

Looking back, our senses of humor didn’t line up as well as they could have. And during the last lesson of Calling in The One, that’s one of the qualities that I identified as non-negotiable.

The essential qualities I’m looking for in a Life Partner:

  • Smart & curious
  • Open-minded
  • Optimistic
  • Honest / communicative
  • Hilarious
  • Active / healthy

I still reeeeeeeally want someone who loves to cook, but I’m willing to sacrifice the thing I talk about most if it means I can share my life with someone who meets all 6 of these completely-reasonable criteria. 

Know anyone like this?? Send them my way! 

It’ll give you something to do as you wait for Part 2…