50 First Dates: VIII

Multi tasking is a challenge. Being everything for others and still being enough for me, is a lot
I often work 15 hour days as a business owner, boss, teacher, student, mentor, coach, daughter, in tandem with looking for love requires effort in all ways — multiple hats worn, atop spandex leotards and stiletto heels. Done up or undone. Self care to me matters most — and I define that simply by sleep, (and sweat), is what I need most. But love will not find me if I stay in bed with email + Netflix, so sleep must be sacrificed, sometimes.


I was late for my date on Valentines Day because I had to run payroll — no follow thruleft me scrambling last minute, And overpaying as a result. Sadly, times like those remind me that sometimes you can only rely on you. Flustered— I rushed into a cab to breathe, + reset, switch off boss life + find softness in the 6 minute drive across town, red dress, red bottom shoes, freshly lotioned skin, and chipped nails.
Starving, I swooped into one of my favorite restaurants, to meet a newish suitor. Sexy. In a black tee, and greaser jacket— his dark features just as delicious as the duck wings I was about to get all over my face. My belly rumbled over the sound of the loud bar, my usual feeding time is well before 8pm. But this was the first time we broke bread, and I let him lead before we we made conversation that lingered too long. after one overproof margarita, zero duck wings (hes pescatarian) and too few too light bites, I could feel my head start to spin. my 100 proof tequila margarita, and empty belly had me digging into the last bits of a cold cauliflower taco left on the table with my hands. my inner savage was roaring — a girls gotta eat. and sure, i could have suggested we order more - but i did not. not his fault, nor mine…just getting to know each other.

I think you can tell a lot about a man by how he orders: the over order is often wasteful, sometimes overcompensating and perhaps overindulgent and im not into over eating and rolling home — to his place or mine, but under ordering can often come off weird, or insecure. so I go for the goldilocks method, not too much, not too little - just right. After three small plates, one cocktail and just under 3 hours of conversation, I was down for the count. We sauntered streetwise — sleep deprived, still hungry, and void of small talk, I grabbed him and kissed him and kissed him again. if heaven has a smell, this might be it - and i told him so, as I grabbed him again. go home with him Olivia., you have no where to be tomorrow morning, go do something sinful for a second. a quick check in with my gut and declined in favor of soft sheets and deep sleep but boy I could have let him ravage me. And in less thinking, more feeling - I opted with feeling. it didn’t feel like the right decision. my bed awaited, but not before a late snack of kale chips, an opal apple and the frozen Momofuku cake ball gifted by my doorman earlier that eve, which I microwaved quickly, and savored slowly. Lights out.


I woke up Friday happy to be in my own bed but lonely as usual. Long weekend, little plans, lots of work. It would have been nice to roll over onto a man wrapped around my body. Wishful thinking as I texted an old fling — one whom ive thought about on and off over the years. we dated briefly but timing was never on our side. And over the years, ive done a good amount of work to recognize and moreso commit to what I want in myself + a man. How can you find something if you don’t know what you’re looking for? text to old fling because ive figured out that i crave a man who both challenges me + supports me. I dont want to lead nor follow all of the time. I want to support + be supported. To love + be loved. To wear the pants + sometimes never even put them on. #balance. My man is strong enough to handle my strength and strong enough to silence it. Enter old fling. 7am text: conference this weekend? Did you end up staying in town? Lets be friends. Quick response: hi, thank you. Can I take you to dinner tonight?
We went back and forth a bit about time + place.
His headstrong vs mine could never find compromise. But maybe timing could finally be on our side.
We settled, rather I gave into his plan of dinner later than I prefer + far too east from my home. No compromise.

Two and a half

If dating is a game of numbers, then im looking to win the game. So I booked a @hinge date prior — to make best use of a fresh blowout + louboutins and hit the town. Im still unconvinced about dating apps but this guy had a kind face, we had mutual friends, and he agreed to meet for a mezcal Negroni on the west side. 45 minutes of dharma talk about life, history, religion, introspection and I had to make my way east to old fling.
I thanked him. We hugged. Not a match.


Eastward bound to kikis for whole fish + a familiar face. I was flustered that they don’t take reservations and there’d be an hour wait - But he surprised me. A table in the back, and he even walked out to retrieve me from my cab— unexpected courtship. We caught up over warm pita + dips about upcoming trips and the element of surprise. come to think of it, he surprised me. But as two Type-A entrepreneurs who believe in themselves and in their abilities, I think we both suffer from lack fo surprise — except perhaps in the one thing you can’t plan, control, or manipulate. love. You just gotta feel it.
he promised he’d get me home by 10pm for a packed Saturday of packed classes @boxandflow.
Graceful as ever I tripped on a step mid restaurant - not a surprise. I saw it coming, but Messy is sexy, sometimes.
We locked lips on the lower east side. His familiarity returned, via kisses years past. I leaned in. And then left — into deep sleep before saturday morning came far too soon. In darkness I made new playlists before lacing up my sneakers. There is nothing that makes me feel more alive than sprinting down silent streets while the city sleeps to take my breath away. Funny enough, in the years we lost touch - we would sprint past each other. Both the same, but going opposite directions. And saturday, as I ran seven miles up the west side, he too was doing the same, along the east river.
Two ships in the night — sailing at similar speeds but with the same intentions.
The question is, can they sail together?

forever seeking balance.
#workhard #livyoung