Double Date, Double Struggle

I was lying on my bed working on homework on a quiet Tuesday evening when my roommate bounds through the door shouting, "GUESS WHAT WE'RE DOING?!?!"
From any normal person I might guess, "Going to the beach" or "Going out for ice cream," but alas with my roommate is was never this simple. Any time I had to guess about something, was a bad sign.
"What are we doing?"
"GOING ON A DOUBLE DATE!!" (yes, this really was all screamed."
Interiorly - I sighed.
"With who?"
"Well you remember Jared*? He keeps asking me to hangout...and well I really don't want to hangout with him by myself. So when he asked me to go out for wings tomorrow night, and I said yes, but I asked if you could come too."
"Okk....."
"Soooo he said he would bring his friend Tim* along! Remember when you met Tim? Well I guess he asked Jared about you.... anyways so Jared invited him, and we're all going!"
"We?"
"Yes, you're coming."
Interior sigh.

The struggle increases and the situation gets a little funnier when the next day, two of our other roommates decide that they will tag along for the date and sit at another table observe.

We decided to drive ourselves so that we would have a quick exit if necessary. Besides, we didn't really know our dates all that well.

We get to the restaurant and Jared and Tim hadn't arrived yet so my roommate and I got a booth and waited. While waiting, our other roommates arrived and were seated a few tables away from us with a perfect view.

We didn't wait for long before out dates arrived. After getting up to greet our dates (and introduce me), my roommate and I sat on the same side of the booth, assuming that the guys would sit across from us. This is normal date behavior right? (Somebody back me up here.) Well apparently Jared (roommate's date) didn't like this because he made a fuss about how she and him were supposed to sit next to each other. Well obviously we were not having any of this so we stayed where we were. Strike 1.

After ordering our wings, we began a casual conversation. Or so we thought. Sigh.
I asked the guys, "So how do you guys know each other?" To which they looked at one another sheepishly.
"Well we met in jail actually," Jared said. Strike 2.
He laughed and it didn't really seem to bother him. I looked at Tim and he looked just a tad uncomfortable.
I pinched my roommate's leg under the table hoping to give her the message: "I'm going to kill you."
(Where does she even find these people?)

Now to give you a picture, I am a nice girl. I wear pink and pearls, do my homework, and go to Mass every Sunday. And here I am, sitting across from an ex-convict covered in tattoos. (I'm not judging. Just get that mental picture in your head.)

Well the date progressed, they asked us about school, what we were studying, where we were from etc. The typical getting to know you questions.
Ok, and I will admit that Tim was actually pretty nice for someone who just got out of jail. (Yes, they were not in jail like 5 years ago. They were just recently - as in a few months ago - released. Strike 3.)
We got out food and began to eat.

While we were eating, for some reason Jared thought it was a good idea to bring up stories about being in jail. I have no experiences with being in jail, and neither did my roommate so we had nothing to contribute to that conversation besides feeling rather uncomfortable. Strike 4.

My charming roommate decides to change the subject with "So Tim, what does the tattoos on your knuckles say?" (Yes, he had tattoos on this fingers like the ones that say "Thug Life")
To which he responds, "Oh, it says Dough Boy.
I repeat, my roommate and I are nice girls, so of course we had know idea what this meant. We looked at each other confusedly. And Jared asked, "You don't know what that means?!" (clearly shocked)
"Um, no..."
He laughed. Sigh.
"A Dough Boy is a heroin dealer." Strike 5.
Double sigh.
Poor Tim, he didn't ask for this either. He said, "Yeah, well I used to deal before I went to jail. Now I'm getting clean though." Awesome.

Continuing on through the date, we hear more jail stories and we are all just real uncomfortable.
The checks come and they don't even pay. Strike 6. They are really struggling. And so are we.

On our way out to the cars, we encounter a fairly drunk woman who asks us for a ride because she fought with her boyfriend. WHAT IS HAPPENING ON THIS NIGHT?!
Jared tells her that we (as in me and roommate) will give her a ride and I want to punch him in the stomach.

I convince Tim to ride with us to the location of drop off because we don't really want to ride with a drunk stranger to an unknown location. We drop her off in an empty parking lot to her ride, and say our goodbyes.

Classy on the outside, struggling on the inside.
At least it makes for a good story.




*names have been changed to protect the dignity of the human person