A few months ago I broke free from an emotionally abusive relationship with my boyfriend.
But after watching a ton of TED talks, scrutinizing self-help books, journaling like it was my job, and all the other cliche stuff you're supposed to do post-breakup, I miraculously felt empowered and normal again. The corny rom-com strategy actually worked.
All I had to do next was conquer the last (but most dreadful) post-breakup assignment: go out on a date. The word "date" made me shudder. Was I even ready to get back into "the scene?" By now, I was so comfortable backstage.
A few internal battles later, I created a dating profile. I hadn't been on a dating app in four years and wasn't sure how to navigate one as a woman in her mid-twenties. So naturally, my mind began racing. Do I pull a pen-pal situation and text the guy for a week before we meet in person? Is it socially acceptable to ask him out on a date or is that too aggressive? Shoot is coffee even considered a date or is that networking?!
Shaking those thoughts, I initiated a fresh batch of copy-paste, "Hey, (insert dating app here) match" introductions. And thanks to virtual convenience, a mere couple of hours later I was receiving so many responses I was concerned my phone would malfunction.
And after a whopping 20 first dates, I can confidently say that each one was unique, memorably awkward, fun, and believe it or not, healing. I learned more about myself dating complete strangers than I had in my long-term relationship. Here's how these 20 dates went down — and what I learned from each one. Note:For privacy, I left out my dates' real names.
Guy Who Wore Hiking Clothes on Our First Date
Thank you for wearing those awesome khaki capris, because I wore my sweaty workout clothes--we were a buzzing match made in Bumble heaven. But to the barista, we were a cringe mismatched duo who were obviously on a first date: you looked like you just came off of a mountain and I came off of a treadmill. And after a fierce shot of espresso, like a typical rebounder, I brought up my ex 10 minutes into the date. Apparently I was more shocked than you because rather than sprinting out of the coffee shop in your REI boots (like you should have), you tenderly offered to help me haul the last of my boxes out of the apartment I had lived in with my ex. But my moral compass refused to take advantage of your innocent compassion (although I do regret not having you help me lug my kitchenware).
This first date that unknowingly jump-started my part-time job of dating, taught me that suitable bachelors actually exist. But the trick is, you have to believe they exist. And that's harder than it sounds because it's tempting to wither away in post-breakup dispiritedness. Oh, and don't bring up your ex to a guy who treats you to coffee and embraces your baggage so much so that he's willing to carry it — literally. I'm such an idiot.
Eager ER Nurse
Clean up in Exam Room 2, because I spit out my ex and the epic backstory of our crumbling relationship 20 minutes into meeting you. I had a clinical aversion to my own advice, apparently. I wasn't able to get my annual Shameful Dating Etiquette shot this season, as the virus struck again when a dumbfounded expression glossed over my face while you (unexpectedly) asked to kiss me mid-date. And naturally, as the ill patient I was, I rejected your kiss because I was fresh out of a relationship. Like, duh, did you not just listen to my hour-long venting sesh?! How dare you ask to kiss a gal who just wanted a therapy session! The nerve.
I'm sincerely sorry, Eager-For-A-Kiss ER Nurse, you didn't deserve the transmission of my rebound virus. But hey, thanks for teaching me that my sick self should stay in quarantine if I still feel compelled to mention my ex (you literally told me that). I learned that my ex is my ex because he EXited my life, so why the heck am I giving him the power to EXert his presence?! It was time to EXterminate him from my immune system.
DJ Who Raves on Mondays
I wasn't sure what was more distracting: your colossal chest tattoo or your monumental sleeve tat (both of which were conveniently on display). And because I was so focused on your skin gallery, I barely remember our conversation. But I do vividly remember that when the waiter came to deliver the check, you looked at me with a casually confused expression and asked, "So... how are we gonna split this check?"
Although it's dating law, sometimes we need to be reminded that if a guy won't pull out all the stops i.e. paying for an $8 meal on a first date (where he should be putting his best-inked foot forward), the rest of the exhibit probably won't get much better.
Unfortunately, like the art apprentice I was, I shrugged and accepted the challenge put forth by this underwhelming, undeserving human Museum of Modern Art. And unsurprisingly, the canvas of our second date was painted with a 30-minute late arrival (his) and the splatter of an attempted luring me back to his place after ordering me an Old Fashioned. His place, ugh, we all know what that means. Good thing we went Dutch (again!), because I didn't feel an ounce of guilt when I flat out rejected his offer in disgust. I should get his lesson tattooed on me (joking) because he taught me that I am the curator of my own life: I can accept and reject any art presented to me, as I choose. But hey, at least our nose piercings complemented one another!
Bohemian Edgar Allan Poet
Our conversation flowed in rhythmic composition. You and I had everything in common, and your wavy, shoulder-length hair and breezy tunic was a physical manifestation of the colorful, creative girl I was before I left for college. I missed her. And what better plot twist than a coffee date that magically morphed into a tranquil session of writing poetry together?! After sharing our most intimate, vulnerable poems of past pain, doubt, and depression, we scheduled our next date at a Spoken Word open mic — apprehensively scanning the poems we wanted to share.
You were magically pulling me out of my stone shell. But alas, our stanzas foreshadowed the screaming incompatibility of our academic and career paths. Our two roads diverged in a yellow wood.
This unconventional man taught me that just because together you're a flawless ballad doesn't mean the two of you are actually compatible. He, Keats and I, Dickinson — our life paths simply missed each other in time. But I'm forever grateful for the tiny slice of creativity, imagination, and hope he instilled in me — I thought I had lost that.
Hello Doctor, or shall I call you Chatty Neurologist, M.D.? You and I bonded over our favorite part of the brain: the prefrontal cortex (the one that controls our higher executive reasoning). But neither of us used it on our first date.
And my hippocampus can only recall talking about our past embarrassing drunk moments, bizarre college stories, and solidarity in considering vanilla ice cream to be inferior without chunks of brownie. In a brief petit mal seizure, I actually forgot you were a doctor (or was that a symptom of the second gin and tonic?! We'll never know...). Because chatting with you was like conversing with a spontaneous, silly, fellow Brain and Behavior classmate. Too bad your pager went off right when I was giggling as you fed me pistachio gelato. Too bad I flaked out on our second date. And too bad (for me) that you had enough self-respect to tell me that wasn't cool.
So hey there, Dr. Neuro, I wish the bell didn't ring mid-lecture. But thank you from the bottom of my amygdala for teaching me to: Treat others the way I want to be treated. I'm sure you're probably prancing in the meadow with a lovely woman who, unlike me, is a way better texter and overall person.
Native American Psychiatrist
For a Psychiatrist, you were staggeringly verbose. I naively assumed conversations with a Psychiatrist were always one-sided (I would know, I see one once a week). As you shared the trials and tribulations of your journey to medical school, I pictured you lying on a recliner looking up at the ceiling, with a notepad in my hand asking you how it made you "feel." Unfortunately, I'm not a shrink and as your self-centered date, my attention span shrunk. I was desperately searching for a "spark," and found myself unable to enjoy the company of the brilliant man in front of me.
And that's when I realized that romanticizing your academic success and career title to the point where I was forcing myself to be attracted to you, was just exhausting and defeats the purpose of what was, above all, a lovely interaction. The lesson to be learned here was just because someone has a sexy profession (and makes more money than any single human really needs) doesn't mean you should trick yourself into being artificially attracted to them. Oh, and for those of you who don't know, doctors are far different outside their office — they're actually normal, attainable people.
Young, Awkward Anesthesiologist
Oof. This one was painful and unfortunately, thus far, most memorable. Out of everyone on this list, you and I dated the longest: over two months. You were by far the geekiest (decade-long World of Warcraft Warrior), uncomfortably awkward (why did you attempt to play with my underarm flab?), quietly confidential (you still remain a mystery) guy to have ever graced my dating planet. But you also had a humble disposition, were charmingly kind, undoubtedly handsome, and compassionately gentle.
Too bad you were emotionally unavailable and (although I stubbornly refused to admit it at the time) so was I. And when we both addressed the inevitable, I cried before you like a little girl who was lost in her own labyrinth of a mind (and in many ways, I was). My disheartened eyes gazed up at your half-baked smile as you kindly let me down. I honestly wish you had anesthetized me right then and there — I wanted to be knocked out of ever meeting you. It was the beginning of Autumn and the rain that drizzled down on our heads reminded me of how nostalgic this time of year is — the craziness of hot summer flings is lost, and we are merely left with a bitter taste of what could have been. We were a beautiful mess. And that night I realized I was crying a little bit for the boy I thought you were and a little bit for the boy you turned out to be. It was a cruel summer.
But above all, you taught me to not date solely for an outcome, but to rather enjoy each other's company in the moment even in the silence of something so simple, like when you would wrap your arms around me, pull me towards your chest and gingerly kiss my forehead.
You also taught me that: Anyone who does not see your value CANNOT be valuable to you.
Maybe we can reconnect in the future. Maybe by then you'll have grasped the concept that not labeling a relationship (that for all intents and purposes, is a relationship) is a disarming tactic. It is loathing the woman who waits in rush hour so you don't have to drive to her after your 24-hour shift. It is an insult to the woman's time — the same woman who rests her head on your shoulder as you gingerly stroke her hair. And it is disempowering because you force the woman who has grown to genuinely care about you, into a position to end something you're not strong enough to end.
Gals, if you ever feel "too needy" because you want to define a relationship, remember this: you aren't "needy" YOU HAVE NEEDS. There's a difference. On a lighter note, we stay in touch and it's pretty freakin' cool (thanks to my ex, my ego now bounces back like a basketball). Oh, I also learned that if you're emotionally unavailable, please do faultless, loving individuals a favor and don't make a dating profile. Seriously. It's just plain mean. Because chances are, she'll lose someone who didn't care, and you'll lose someone who did.
The First (and Last) Woman
Let's put this in equation form: your badass personality + chocolate skin + baritone voice + 5 hour date = magnificence. Divided by me = forever lesson: I am not a lesbian.
My Friend's Ex
The lesson I already knew, no, the lesson all functioning humans already knew. But I guess I had to press my hand on the burner to see if the scorching held up in reality. And as uncomfortable as I am admitting to this: never date a friend's ex. It will always be awkward and you'll feel unethical forever. I was left with fourth-degree burns of guilt.
(Super) Tall, Shy East-Coaster
I think being able to, without your interruption, sit in the car at midnight listening to Taylor Swift's new album is hands down a successful date. I was embarrassed that my high school idol's petty lyrics are relatable, but you were so sweet to not judge me. Rather than poking fun at my guilty pleasure (which you totally could've done, because track no. 3 was mediocre), you made me feel like even the dorkiest aspects of myself can be honored. Maybe a fine friendship could ironically be forged in an un-kosher way: off of a dating profile of merely three pictures and a one-sentence blurb.
My new friend taught me that friend-zoning a guy doesn't mean that our dates in dark movie theaters, competing over the loudness in a bar, or sweaty palms and nervous laughter weren't a success.
In actuality: Sometimes a budding friendship can be one of the most profound successes of dating. So thank you, Tall Shy Guy From the East Coast, for teaching me that it's OK to enjoy an awesome date even if it's lacking in romantic chemistry. I'll listen to T-Swift with you any day.
Yεια σας (that's hello in Greek). You and I were Hades and Persephone... rebels. We met in the pouring rain, in the dark, at 8 p.m. on a Wednesday, yet we bravely shared an ice-cold cocktail. As the two of us sat outside on freezing metal chairs all bundled up, the rain cascaded down from the sky like boulders. Each drop was cleansing as if it were washing away the past and clearing the way for a fresh start. You were a recent transplant from Greece, your starry eyes in pursuit of an American Ph.D., and although your accent was foreign, it was soothing like the final drops of rain just before the sky cleared.
Even though I make a daily, active effort to be open to new cultures, I've always had a difficult time relating to people who grew up vastly different from my "norm." But this Greek guy from overseas taught me that just because we grew up in different cultures, doesn't mean we can't relate to each other. To my delighted surprise, we shared the same values, beliefs, and morals. And nothing on a first date can feel more like home than that.
I can't wait to hear all about your trip home to Greece next week. I'm totally envious!
Argumentative Aerospace Engineer
Do I regret being text-pals prior to meeting you in person? Perhaps. Through hours of exchanging heated text messages on differing political views, I could tell you were an intense person — just like me! We both knew our first date had the high potential of being a lethal combination of strong opinions. Luckily, we ended up chatting (conflict-free!) for hours over Moscow Mules.
Your fervent argumentative personality was surprisingly intriguing because with it came passion. And I could hear the intensity in your voice as you discussed the satellite you were designing for a snazzy aerospace company founded by Elon Musk. It was the first time in a long time that I felt like an idiotic newbie on a foreign subject. Yet to my delight, I was desperately thirsty for additional knowledge on this supremely niche topic I had never thought twice about.
What an incredible lesson this brilliant man taught me: Just because you don't have much in common, doesn't mean you have nothing to talk about. In fact, you can have endless conversations and grow a few new neurons in the process.
Perceptive Rock Climbing Computer Engineer
What a beautiful person (both outwardly and inwardly). You are a superhero who programs by day and boulders by night! You're also a self-identifying intersectional feminist and a person of color (just like me!). That's like hitting the jackpot if you've ever attended a Liberal Arts college. We understood one another at a spiritual level. Remember how we gazed into each other's eyes over over fish and chips on the shore of Lake Union just as the sun disappeared behind the mountains? The coral sky smiled above us as we formed a bond of solidarity that I seldom found prior to meeting you. I felt safe enough to admit that I'm going through a tough transition right now.
Your compassion taught me that even though life hasn't been easy, my resilience is never a disability. It is actually one of my most attractive, powerful features. No one should ever hide or feel ashamed of her past, because that's what makes us so powerful in the present. Resilience is beautiful, let's celebrate it. So hey again, Perceptive Rock Climbing Computer Engineer, I'm excited to cultivate our friendship.
Older, (Divorced!) Guy
I guess we clicked because our conversation flowed as smoothly as the wine. Because you, Mr. Grown-Up, were married in the past, you knew exactly what you wanted in a woman, and were crystal clear in your intentions. My usual millennial dates tend to avoid any talk of commitment (*cough *cough: "situationships," "ghosting," "breadcrumbing," and "stashing"). Your direct pre-marriage interview approach was by far the most refreshingly foreign date I had ever experienced (more foreign than Greek Physicist!). There's something compelling and just darned attractive about a man who knows what he wants. And even better — a man who can communicate it effectively.
And this leads me to the most awkward question I thought I'd never have to ask myself: older men have their sh*t together, but do I?! Apparently not because moronic millennial me fled from him like he was Michael Myers. But hey, an outstanding man who would make a great life partner and father — catch me in 5 years and I'll be ready! *Cue nervous laugh.*
Jewish Guy With 40k Instagram Followers
Shalom, fellow rare Jewish Pokémon — there aren't many of us out there! And I could tell you were eager to meet a PikaJew like myself because I don't think anyone would casually mention he postponed his dental appointment (and yes, your tooth bothered you during our Italian dinner), and Ubered 20 miles to see me. I felt like a Mewtwo who was swiftly captured by your poké ball. You know how to catch 'em, because your stats included: world traveler, graduate degree in Bio Medicine, Software Engineer of your own company, Mathematician, acroyoga king (if you don't know what acroyoga is, look it up — you'll feel like a lazy P.O.S.), and over 11 million views on your Linkedin. Oh, and not to mention you did a TEDtalk. Let's just say you made me feel like a degenerate.
But, Jewish Ketchum, you did teach me the valuable lesson that nobody is ever too busy to date. You made time to see me. "Too busy" is social construct, and a euphemism for people who have time to watch mediocre Netflix movies, browse Instagram "models" butts and play video games for 4 hours straight, but are otherwise "too busy" to date (but, of course, not too busy for a wham bam thank you ma'am!).
Because let's be honest: Nobody is ever too busy to get what they want. Thanks for making me feel special. But my XP is lower than yours. I'll never measure up to you.
Smiley Ivy League Guy
By now, dating had become a sport: the more I practiced, the quicker I became at cutting to the chase. So I thought, hey, Ivy Leaguer, let's skip the awkward menu-scanning and subtract the noisy bar. Instead, I suggested we meet at the grocery store, where we grabbed a bottle of wine and some sandwiches. As we headed for the lake, we realized how amateur we were and had to make a pit stop at the local drugstore for a wine opener. But that didn't stop our date! We power-walked to the local park and just as I planned it, we were able to have a heart-to-heart while gazing at the sunset in the distance, as the rays sparkled on the lake. You and I shared a moment frozen in time: two complete strangers who would otherwise have never crossed paths, silently admiring a magical moment.
But throughout the date, you alluded to us having future dates, which was when I realized nobody is ever on the same page with dating unless it's made clear. The mere idea of a future terrified me, which was probably why I anxiously grinned and said, "sure" whenever you brought the topic up. All this dating had upped my acting skills.
The takeaway from this one: Mr. Right may exist in the distant future, but Mr. Rightnow can appear as a fleeting tipsy five hours. Sometimes we don't need commitment, future plans, or weekly date nights with the same person to feel fulfilled. Sometimes people are meant for us, even if for a mere cameo in our ongoing lives. Maybe someone could be "meant for us" even if we don't wind up together. I still anticipate our bi-weekly morning platonic coffee dates. With you, I don't need caffeine to start my day with a smile.
Hot Long-Haired Lifeguard
OK, this is where I confess that I can be shallower than a kiddie pool. So let's just put it on the table that because of your tan body, abs, and model-like face (all of which were conveniently on your profile), I immediately "swiped right." But this is reality, not "Bay Watch," so when we met up for Thai food, I couldn't help but wonder if you knew your awkwardly nervous, bashful demeanor was the inverse of your physique — which made me feel comfortable to swim this date with you.
After our tummies were filled with pad thai, we walked to the playground where you spun me on the chilly metal merry-go-round, winding down with a swing on the swingset in the drizzling rain. I weighed out my risks and decided you weren't a serial killer, so I invited you home to meet my cats (that's a compliment). And LOL, because you (accidentally) ended up also meeting my mom. You poor thing.
At this point, seeing how easy it was for me to admit you into my life so casually, I realized I wasn't interested in anything serious in any of the guys I dated. Because if I were, this double-whammy cat and mom introduction would've been planned more strategically. And for the first time after all these seventeen dates, I was upfront and told you that I wasn't interested in a relationship.
You taught me: Being honest about dating intentions isn't just being kind, it's being ETHICAL. I love how we keep cat and mom visiting an ongoing thing.
Stoked Elevator Builder
First off, thanks for introducing me to the Elevator Builder Union, because they sound dope and now I think everyone should get a Union job for the benefits. Secondly, no thanks that you planned on introducing me to your closest friends on our first date. You were hyper for someone who came from a southern town, population less than five hundred. Plus, your loud enthusiastic laugh was only slightly terrifyingly unexpected. Your voice could even be heard over the thunder and lightning storm hitting the metal roof of the Mexican restaurant.
Sorry dude, but I had to cut our first date short because you quickly taught me that:
If the date isn't moving toward another date, it's better to end it sooner than later so you don't waste each other's time. As the elevator ride of our date reached the ground floor within two hours, I couldn't help but push the "open door" button. But OK, I'll admit that it was sorta cute how you asked to hold my hand. And if we're being honest: our two hours wasted was kind of fun!
Handsome Singaporean-Italian Guy
Half Italian, half Singaporean is a darn good mix. But how did our first date become a bad mix? Well, that's one part my unpunctual arrival and two parts my dreading our first date. Poor guy, I thought, as I trudged into the restaurant all fired up. Ten minutes prior to greeting you with the generic, insincere, "Hey! Sorry I'm late," accompanied by an uncomfortable smile, I had rage-deleted all of my (2) dating apps. My fed-up ego had reached its pull date of keeping track of 15 ongoing text messages, round-the-clock worrying about hypothetical mixing up names, and anxiously anticipating the seething replies from three guys I had rejected earlier that day. Let's get this last one over with.
But somewhere in the depths of my hippocampus, I remembered Chatty Neurologist who, a month prior, taught me to treat others the way I want to be treated. I didn't want to treat you as disposable. And go figure, because a mere 30 minutes later over garlic-infused Taiwanese pork belly, a sprinkle of sentimental smiles, and a dash of anticipation, I swallowed the tabula rasa of a gentleman one bok choy plate away from me.
And less than 48 hours later, we had our second date. And less than 24 hours after that, we had our third date. Oh, and there have been many more since. So hey, Handsome Singaporean-Italian Guy, thanks for crushing my preconceptions. Maybe I'm ready for commitment after all.
But this is freakin' reality, hopeful girl, and just like I predicted, you and I inevitably weren't a good fit. I felt unrefined as a passenger in your spotless white Audi (with orange leather) and like a puerile insult to your lifestyle as a Senior Product Manager at Amazon who owned a snazzy condo.
I'm a little crude, cynical, and unpolished, but I embraced your divorced past and felt vulnerable enough to share my wild trials and tribulations in return. I should've just kept my mouth shut. But I understand that your guarded heart was scarred by your divorce, as you were clearly on the hunt for a mild, safe option of a new wife. And when I scared you (yay, just in time for October!), with stories of my past, you dropped me like a bad habit.
I am by no means perfect, but I gave you unapologetic understanding, warm acceptance, and naively reached my hand out for the same — but instead, you handed me the wicked lesson that I should never open up my heart in the early stages of dating. But, Handsome Singaporean-Italian Guy, I have so much love to give and am a wonderfully committed partner, and believe it or not, my crazy past has raised me to be that woman.
I sincerely hope you find a lady as devoted to you as you are devoted to moving forward post-divorce and finding the "perfect" second wife. But remember this as you date new prospects: Lessons come from outside the comfort zone and the worst that can happen will ALWAYS be a lesson. Long story short: I'm a Four Loko and you wanted a White Claw.
The lesson: it's one that I kinda knew all along, but (apparently) needed some help from others to figure out — I will always be the most important person I'll ever date.
Two hectic months and a whopping 20 first dates later, I can honestly say I have experienced the strangest, most awkward, hilarious and down-right awesome dates I've ever been on in my entire 25 years of existence.
But above all, I have learned that finding "Mr. Right," dating him, and vowing to marry him will never leave me fulfilled if I don't continue to date, and vow to marry myself. So if there's any woman, man, or non-binary identifying person out there who read this one-heck-of-a-long-ass-article and wants to know my biggest takeaway —what we all ought to do — it is to (literally)stand in front your mirror and look really hard at yourself (especially guys #14 and #19, since ya'll have been married before), because that's who you're gonna date and be married to for the rest of your life.
Look at your face first, then your body. What do you see? For me, I see uneven eyebrows, crooked eyelids, and a zit smack dab in the middle of my freaking forehead. But I also see beautiful almond eyes, a toned body, and a charming smile.
Now, look a bit further, past the physical stuff. What do you see? When I stare at myself for long enough, I slowly begin to see a woman who is in-between wanting to swing on the monkey bars and wanting to swing into her career.
OK, now look at what you have to bring to the table on a first, second, third date. What do you show up with? Well for me, that's baggage stuffed with three cats, a lifetime of battling depression, external and internal scars, and a guilty pleasure for mediocre horror movies. But if I dig deeper, I also carry lessons that I can teach you, a resilience that I can share with you and a witty sense of humor that may make you snort with laughter.
So now that you've gotten used to looking at your kick-ass self in the mirror, take a deep breath and get super-dee-dupery excited, because this is the awesome, brilliant, funny and hopeful person you'll be dating for the rest of your life. In fact, this is the person you'll be married to until death do you apart, whether you like it or not — no divorce allowed.
And thanks to the past couple of months, I've learned to consciously fall in love with myself, even if there isn't an M.D. after my name, stay with myself even if I ranted a little too much, hold my hand by my bedside during times of depression. To love myself, treat myself, and talk to myself the same way I would want my partner to.
So hey there, reader — it doesn't take 20 first dates in two months to realize that dating and marrying yourself will be the most important relationship you will ever have. Because if you can have the time of your life dating yourself, simply adding another person to those dates will only fulfill you (and them) even further.
Accept who you are, as you are, RIGHT. THIS. MOMENT.
Because if you can love yourself for who you are, as you are, right this very moment, you can also love others for who they, as they are, right this very moment, too.
And maybe that's what dating is all about?
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