Greatest Strength -- CEO, lead designer, Unquestioned God-Matriarch of the bridal hair accessory megaconglomerate, Hair Comes The Bride
Weakest Weakness -- Potential business connections have become so scarce that she is forced to seek out exposure for her beautiful hair accessories on unrelated pasta blogs
Feelings about the Olive Garden -- [Before eating] "I...don't think I'd accept a date here." [After] "This is surprisingly good."
Snapshot:
After a brief awkward exchange, Gina gets up to 'go to the bathroom', and since she takes her purse with, I assume she's leaving for good. To my pleasant surprise, she returns shortly after! I ask if she had trouble starting her car.
"Mm. Triple A's on the way."
Creative Challenge -- "Write a haiku that contains the word 'tickled'."

Result:

(Transcript)

Tickled by my meal
The company was the best
Pick me to win please

--

It's great to find someone as positive and bouncy as Gina. Often, these qualities are tied to a tiring ditzy-ness (and this is true of both men and women), but she is savvy on top of being fun to talk to. Also, since I plugged her store, I expect full cross-promotion in the form of a breadstick tiara in time for my wedding.

Vino's Vegan Victual:
8/50

Gina's Grub:
Event Horizon

42 dates to go! Thanks for dining with me, Gina. You go, girl.

Greatest Strength -- Fearless nature led to perhaps the greatest heist in Olive Garden history (see Snapshot below)
Weakest Weakness -- Easily distracted; finished maybe 1/10th of the stories she started
Feelings about the Olive Garden -- "I'm ambivalent. Oh. Once I came here with my mom, and her friend, and her friend's daughter. Anyway. We had a waiter named Quest. I'll never forget that." (editorial note: I have no idea if this was a joke, or a reference, or something of that nature -- I leave the interpretation to the viewer)
Snapshot: Throughout the date, Lu continually flirts with our waiter, each time getting him to bring back more and more shrimp (which she barely touches). Watching her work her craft enthralls me. There's something deeply primitive about the way the waiter returns again and again, overflowing her salty ocean shrine.

By the time we leave Olive Garden (half an hour after closing time), Lu has bilked Olive Garden out of 23 shrimp and a colorful cloth napkin, which she repurposed as a trendy scarf that really tied her whole outfit together.
Creative Challenge -- "Write a limerick than contains the word 'camera'."

Result:

(Transcript)

I once went on a date from Reddit
& my God I wanted to end it.
I struggled with rhyme
The whole FUCKING time
I tried but in the end I didn't.
Camera.

--

Lu was a gamble that paid off, and not just in ill-gotten toppings. She found me through a post I made on Reddit.com, an internet message board famous for its campaign to make Bernie Sanders so popular that Hilary Clinton would lose the race for the presidency (WE DID IT, REDDIT!).

As you may expect, the clientelle of this site is all over the place. That was my original point. So a date with a redditor can, potentially, be just about anywhere on the scale. This one was right up there at the top. Lu has the "demure exterior, sharp-tongued interior" thing down pat. One minute she's giggling coquettishly, the next she's tearing your heart out and mocking your height.

Not that I'm even sensitive about that. I don't know how much more clear I have to be. I must have said so, like, five times.

Vino's Vegan Victual:
7/50

Lu's Larceny:
The Ocean Called!!

43 dates to go! Thanks for dining with me, Lu -- and it's not like you're that tall, either, y'know.

Greatest Strength -- Finely-honed nose for news enabled her to get in on the ground floor on what will assuredly be the pasta blog/reality tv dating game show hybrid of the season.
Weakest Weakness -- Fierce independent streak which involved a week-long phase of referring to herself as "Xoie"
Feelings about the Olive Garden -- "I love it! When I lived in Orange County there were not that many unique or interesting places to eat, so I fully embraced the chain restaurant lifestyle."
Snapshot: As usual, I explained the concept of the date's Creative Challenge, and its purpose, to Zoie. When I completed my summary, she smiled, picked up her pen, and brightly chirped "Wow! I hate this!"
Creative Challenge -- "Write a haiku that contains the word 'breadsticks'."

Result:

(Transcript)
Alyssa gave breadsticks to-
go. She's the greatest
waitress in OG history.

--

Zoie works for Los Angeles magazine and, since she was "assigned" to me as if I were a natural disaster, must have a boss with a sense of humor. I usually play the interviewer role in my dates, so it was a weird change of pace to be asked so many pointed questions about Olive Garden that went beyond making polite conversation. It gave me a new sense of empathy for the women on the other end of the salad bowl, that's for sure.

Vino's Vegan Victual:
6/50

Zoie's Zupper:
Hoplite

44 dates to go! Thanks for dining with me, Zoie - I know you'll get that big scoop one day!

Greatest Strength -- Crafting D&D characters that have a tragic backstory reminiscent of a Game of Thrones antihero, but different enough to not be sued by George R.R. Martin (yet)
Weakest Weakness -- Brought shame upon our table when she misheard the options of 'soup or salad' as "Super Salad" and tried to order it
Feelings about the Olive Garden -- "I love the breadsticks. I was just talking about them with my Uber driver, we bonded over it."
Snapshot: Feeling a little constricted by my creative challenge format, I asked Crystal if she had any other creative talents she could comfortably display in a booth in an Olive Garden. She suggested music, tempting me with this: "My singing is like...really, really, really, really shitty Amy Winehouse."

"Ah..." I replied. "Well... for now, what's your second-favorite cartoon?"
Creative Challenge -- "Draw Mojo Jojo from memory"

Result:

(Transcript)
Bootleg
Mojo jojo

A HAND

--

Equally at home in an obscure anime cosplay or sharpening some corporate tool in her work as a consultant, Crystal is the sort of renaissance millenial that is single-handedly ruining our country, according to Parade magazine. She's the rare kind of person who is considerate in a way that feels genuine without being obsequious. Anyone can read a guy's pasta blog (though many, for some reason, do not), but few actually go to the lengths that Crystal did in her helpful and positive feedback.

Vino's Vegan Victual:
5/50

Crystal's Concoction:
Gravity Well

45 dates to go! Thanks for dining with me, Crystal! I hope you were able to find your way home!