Greatest Strength -- Making uncultured midwesterners uncomfortable by forcing them to guess how her name is pronounced (pro tip: SOH-null)
Weakest Weakness -- Unpriviliged upbringing (ie, not in America) gives her the mistaken belief that this is not the greatest country in the world. Tragic...
Feelings about the Olive Garden -- "It's not very good. It's very heavy. And expensive. And not a good place for - " (I cut her off here and changed the subject)
Snapshot: In order to establish dominance, Sonal asks me how many tinder matches I have. When I tell her, she kind of smirks and then gives me her phone, revealing over 60 times as many matches as what I thought was a respectable count.

Okay, she's attractive, I get it. What kills me is that she gets all these guys and doesn't even have a pasta blog. What am I even doing, here?
Creative Challenge -- "Draw a chicken, and two chicks."

Result:

(Transcript)
A Chicken & Two Chicks!
Sonal

--

Sonal is a highly educated (3 degrees!!) woman with a dry sense of humor. I'm not entirely sure about those credentials, though -- she told me that they were two masters' degrees and a bachelor's in psychology, with a minor in art. But after finishing the creative challenge (above) she looked at it, looked at me, and said, "Well. I more meant that I appreciate art."

Vino's Vegan Victual:
4/50

Sonal's Supper:
A Chicken & Two Chicks!

46 dates to go! Thank you for dining with me, Sonal! You get +1 point!

Greatest Strength -- Owns three games for the Nintendo Switch, which accounts for 150% of the system's playable library.
Weakest Weakness -- Overly agreeable nature leads to accepting propositions for mundane first dates (see below)
Feelings about the Olive Garden -- "I think this is the first time I've been here since college."
Snapshot -- Ever the gentleman, I offered Jessica a rare glimpse into the brief non-pasta portion of my day-to-day after dinner.
"Do you want to help me buy garbage bags at Albertsons? I'm all out. This isn't code for anything. I'm literally going to Albertsons and buying garbage bags, then I'm going home."
Amazingly, she accepted, and was an insightful companion for this task. She noted the relative cost-per-bag of various brands, and weighed the value of certain features. Vanilla fragrance, puncture resistance, that sort of thing. In the end, I walked out with the optimal garbage bags, thanks to her procurement skills.
Creative Challenge -- "Compose a haiku that contains the word "salad".

Result:

(Transcript)
Vino* orders salad
It looks to be quite tasty
Why did I choose soup?

(*Transcriptor's note: Jessica chose to use my christian name in this poem, which I do not recognize from the dates of 9/25 to 11/19. I have replaced it here, but I assure you the meter and syllable count remain unchanged from her original poem)
--

Jessica is a procurement specialist for a company that manufactures computer motherboards and similar technowizardry things. She gave me an insider tip that soon 7-11's may feature digital touchscreen displays for their famous Slurpee machines. Personally, I cannot think of an interface less suited to the human hand than a machine that blorps out a thick, sticky sludge directly onto the user. But I'm no computer jock, and I'm certainly no procurement specialist, so I'll leave it to the professionals.

She also agreed to a brief second meeting when I realized that we forgot to get a selfie. Rookie mistake on my part. I been out the game too long.

47 dates to go!

Vino's Vegan Victual:
3/50

Jessica's Jam:
The Mixup

Thank you for dining with me, Jessica! You're rad.

Greatest Strength -- Tough to narrow down; when I started to ask if she was the best at something, she corrected me: "the *greatest*"
Weakest Weakness -- Drive for perfection in her poetry led to most of the date being her groaning at the heavily-scribbled page in front of her
Feelings about the Olive Garden -- "I think I might have come here when I was a child? That may be a false memory."
Snapshot: The traditional end-of-date selfie is taking a little longer than either of us would prefer, with challenging lighting conditions and my hair not being just so. Eventually, Emily asks if "anyone has ever compared these pasta dates to a prison".
Creative Challenge -- "Write a limerick that contains the word 'pumpkin'"

Result:

(Transcription)
There once was a man quite drunken
Who was saucily eyeing a pumpkin
In a manner quite sloppy
And somewhat too floppy
Humped it until it turned sunken

--

Emily prides herself on her numerous positive qualities, as well as her flaws. Her biting wit can be a little off-putting (you should see the first draft of her limerick, which got pretty personal IMO) but she is a joy to converse with, if you can keep up.

Incidentally, her job is way more likely to be automated than mine, despite what "everyone knows". Just putting that out there. I'm gonna be fine, okay? Okay?!

Vino's Vegan Victual:
2/50

Emily's Edible was
A Big Bowl Of Cheese Puffs

48 dates to go! Thanks for dining with me, Emily. You are very charming.

Greatest Strength -- Much like a homing pigeon with a part time job, Leslie can always find the most direct route to a Target from an arbitrary starting point.
Weakest Weakness -- Sales on spooky halloween pajamas
Feelings about the Olive Garden -- "I don't know. I'm not picky. If somebody wanted to go here, I'd go."
Snapshot: "I'll take the breadsticks," I offer graciously, placing them in my bag before Leslie has a chance to ask for one. "I can give them to my cowor-"
Her demeanor changes before I can even finish my sentence. "DID YOU SAY CORGIS??"
"N...no. Coworkers."
"Ahh.....I love corgis, though."
Creative Challenge -- "Draw a Pikachu from memory."

Result:

(The marinara stains are my own. I apologize deeply for my desecration of this art, and I pray that the audience will not hold the damage against Leslie when determining this year's victor)

--

Leslie is a college student studying geography, and she was a very good sport about my pointed questions about the career options of a field that has been obsolesced by the existence of the humble GPS. My smugness evaporated, however, when both of our phones died simultaneously, and the waiter asked us what the capital of Turkey was, and what was the difference between a basin and a plain.

Vino's Vegan Victual:
1/50

Leslie's Lunch:
Creamy Mushroom Sauce

49 dates to go! Thank you for dining with me, Leslie! You were great!