M: I’m on a boat! No, wait, I want off…

Context: After ages, no, MILLENIA of swiping right on any decently attractive human with a picture on a sailboat, I found a guy with his own boat nearby – JACKPOT! ‘Sailor’ and I chatted for a bit before we set a date to go sailing up near Annapolis. The week we were supposed to sail, he messaged me about getting drinks first. I agreed, thinking it made sense to do some due diligence before spending an entire day with a potential axe murderer (haha, kidding! kinda!) alone out on the Chesapeake.

His work friends joined my roommate and I at a local favorite – happy hour at La Tasca (this restaurant should seriously be paying us for all the press they get on this blog. Are you reading this, La Tasca?! We DEMAND free sangria and empanadas!!). La Tasca was, as always, a huge hit, and his friends were cool guys (J actually fell in love with one of them and has been planning their wedding ever since … I’m looking forward to this bachelorette party). In fact, I spent most of the time talking to everyone except him. Cool friends, not too awkward, I was in for sailing. But, tbh, I was set on going unless he gave off that I-will-kill-you-with-my-many-weapons vibe.


After happy hour, I was catching up on some work in the living room while J baked pumpkin muffins (aka positioning myself strategically so I could lick the bowl as soon as the batter went in the oven). Sailor sent me a text, asking if he could call. It looked like a while before that pumpkin goodness would be ready, so I gave him the affirmative. He called, and spent the next hour playing me bits and pieces of songs on the guitar over our terrible phone connection. I couldn’t really hear anything, but he was trying! How sweet!

I woke up beaming on Sunday morning, not so much because of ‘Sailor,’ but because of my true love: his Catalina 22. I hopped on the Metro to meet him in Bethesda for the ride up to Annapolis, hoping the weather would hold up. It did! We had a pleasant drive, picked up some rum from the liquor store, and made the trip to the marina. We got the boat out, and I ran the jib while he steered. An excellent day of sailing, if you ask me! We went to the boat club’s restaurant for dinner and made a meal out of crab dip and soft pretzels. *What dreams are made of*


Things were looking up… until we stopped at his parents’ house to drop off the cooler he’d borrowed. His dad, a very nice man, was waiting and ready to talk my ear off and swap stories with his son. Okay, homeslice:

  1. Why am I meeting your father on the first date?! We are NOT in high school anymore, and we met on TINDER, and the only thing I know about you is that you have a boat. And a father.
  2. Um, it is late, and I have work tomorrow morning. Once again, not in high school. I can’t just nod off through first period tomorrow. I cleared my throat loudly to get my point across, and he finally got me home around midnight with promises for a second date.

Unfortunately, my sailor turned out to be a one trick pony. His suggestion for a second date (third by his count – who knew our happy hour date where I didn’t talk to him counted? Learn something new every day!) was to go up to his parents’ house, do some work on the boat,* get some laundry done,** and spend the night at his parents’ house.


“?!?!?!?!” you may be wondering. Trust me, I was as well. The answer, ladies and gents? Because it was “convenient for him.”  Issues:

  1. Dude, you have your own apartment and you’re asking me to spend the night at your parents’ house?! Omg maybe he is still in high school. Send a pack of #2 pencils and some help ASAP.
  2. Convenient*** for YOU, maybe, but what about me? I am important, damn it!!
  3. Do you honestly think my ideal Saturday night involves helping you do laundry and hanging out with 50-year-olds, who think that I am their son’s eternal lover, when in reality we’ve been on ONE DATE?

*Not sail it… do work on it. FUN.
**Sorry, am I your wife? I wasn’t aware. Do we have kids I should know about, too?
***Dating is not supposed to be convenient. It is supposed to be fun, and mildly stressful, and give you all those butterflies and electricity and backflips in your stomach. If it were convenient, everyone would do it! Well, all the pretty people, at least *hair flip emoji*


Look, I’m all for family bonding time. I happen to be very close with my family, too. But this guy is suffering from a severe case of “my mommy still does my laundry” syndrome. I politely declined; I believe the exact wording was “um wtf, no I barely know you.” Which then led him down the rabbit hole regarding where he saw “us” going and how he was looking for a “serious girlfriend.” Excuse me, are you trying to DTR after our FIRST DATE? Shudder, cringe, hyperventilate.

For some reason, still unbeknownst to me, I agreed to a rescheduled second date on Sunday night. The plan: he would cook me dinner at his place (wow, he DOES have his own apartment! Who would have known?!) because he is a “really good cook.”

Just in case y’all are like, why is this psychopath not yet kicked to the curb, I REALLY love sailing. He owns his own boat. I have needs, guys.


Okay, so I know I’m breaking my rule of all dates in public places, but he’d already had the chance to kidnap me while out at sea, and he didn’t, so I figured I was in the clear. I made the 40-minute metro ride to Bethesda for what I expected to be a delicious home-cooked meal. He’s from Maryland, so there would definitely be crab cakes and Old Bay involved. Ooh, and perhaps a dessert. After all, he wants to pull out all the stops to impress me, right?

When I finally got to his apartment, the fish was in the oven, and he had laundry to put away (for fuck’s sake, HOW MUCH LAUNDRY CAN ONE BOY HAVE?!).

I had the time of my LIFE sitting on his bed and making small talk while he cleaned his room. Really, truly thrilling. To top it off, his bedroom trash can had a used condom in it! Ooh, looks like our little “serious girlfriend” seeker is testing the waters (see what I did there?) with multiple ladies. I called him out on it with a casual “hey, has it been a while since you emptied your trash can?” He looked puzzled and replied “um no.” Then, the look of realization hit and he fell to his knees, proclaiming that he felt “so guilty.” I’m now bracing myself for an “I’m cheating on my girlfriend with you” or something along those lines, but nah. He’s just “dating” two girls at once. However, he was very clear that “things are looking good” for me.

AWESOME. Glad to know I’m winning!!! But I’m starting to think that if you’re the prize, she can have it. Good to know you’ve used protection with previous partners, though!! You must have gotten (should still be getting?!) an A+ in high school sex ed!


Finally, our gourmet dinner of frozen fish and Ready Rice was done. Great job, “really good cook!” You really blew my socks off, you must have spent hours picking out the best options from the freezer aisle!

It gets better – his plans for after dinner consisted of him serenading me on his guitar and me trying to keep my eyes open after an exhausting weekend of other Tinder dates. At this point it’s Sunday night, I want to be in my sweats watching Friends re-runs, drinking wine, and swapping date horror stories with the girls not stuck in the middle of one. My sole mission was clear: convince Sailor to drive me home. He either still felt guilty about his “other woman” situation, or I’d been too obvious about how much I hated this date, because upon dropping me off he promised to take me somewhere ~*fun*~ next time. Oh, joy, next time (yawn).

I took a step back, reflected on the good time we had sailing, and psyched myself up to try again. I was excited when he suggested we go to a concert on Wednesday night in DC. Concerts! Fun activities!


On Wednesday morning, I probed him for the details. So, the concert’s actually in Bethesda. Is anyone surprised? Like, DC probably wouldn’t be convenient for him, and we absolutely can’t have that! Also, it’s the Navy band concert: think stuffy formal concert hall and nice attire, not a chill evening with some rando low-key band. I was becoming less and less excited by the millisecond.

I suggested that I could go straight from work since I was dressed up anyway and already in DC, plus we could grab dinner beforehand. Well, silly me, it completely slipped my mind that Wednesday is taco night with the guys! How on EARTH could I forget?! But, him being the kind soul that he is, invited me to join them. When I mentioned I didn’t eat beef, he suggested rice tacos. DELISH! His other suggestion was that I pick something up for myself, then come over. Brilliant, I REALLY wanted to pay for my meal and eat alone. Great date idea, Sailor.

At this point, the date had started to become far more effort than it was worth. I wasn’t up for going all the way out to Maryland for some stuffy formal concert and having to buy my own food. Hard no. I sent him the “my manager just gave me a ton of work at the end of the day OMG how could she I was so looking forward to the French Horns!!!” text as I boarded the metro to head home, relax, and enjoy my more important date with my three favorite men: Chandler, Joey, and Ross. (Actually I hate seasons 3-5 Ross, maybe its because he reminds me too much of ‘Sailor’?)

Now, if my Sailor ever comes through on his offer to take me sailing into Annapolis where we’ll eat a NICE dinner and explore the city, I will go. Otherwise, I’m fully prepared to do… The Fade Away.

❤ M

Posted in M

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