Day One   /   lettering by Keetra Dean Dixon

Jessica Walsh

Did you see Timothy today?

What did y’all do together?
We had our first date at The Fat Radish in the Lower East Side. They have the best roasted carrots, and my favorite tequila jalapeño drink.

Did anything interesting happen?
Before the date, Tim had a messenger deliver a cute note: “Me + You x 40. Ready?”


Truthfully, I am quite nervous. However, I know that when an opportunity scares me, I must go for it. I don’t like having fears. No matter what the outcome, it will certainly be an interesting experience. Hopefully we can have some fun along the way, too.

Did you learn anything new about Timothy?
We discussed Tim’s relationship patterns, and how he’s in a constant cycle between three women. There is always one girl he’s really excited about that he’s trying to go out with, a second girl he’s been seeing for a few weeks and is getting tired of, and a third girl he’s been seeing a while and is getting ready to break up with.


He told me that when his mother got pregnant, his father made her choose between keeping the child or staying with him. It seems to me his dating style could result from this. He breaks off relationships before they get too serious to avoid the risk of abandonment. He’s built up this reputation for himself as “the player,” but I see past the façade. He’s been a great friend, and I know he’s a very kind person. We all have our issues and cope with life differently. Sometimes I think the “normal” people are just people you don’t know well enough yet.

Did you learn anything new about yourself?
We talked about relationships with parents, and how many girls have “daddy issues.” I don’t have dad issues. I heart my dad!

My parents married at a young age, and have a successful marriage. I wonder if that is part of the reason I am always trying to find the right person and why I feel like such failure when a relationship doesn’t work out.

How do you feel about this relationship/project right now?
I think I have have some sort of guard up preventing myself from seeing Tim as anything more than a very close friend. As his relationship patterns are the opposite of mine, a part of me fears that if we were to really date, one of us might wind up getting hurt. I don’t want to ruin our friendship. We also have a tight group of friends, and I think we are both afraid to compromise that.

Is there anything that you want to do differently?
In my work and other aspects of life, I am uncomfortable with comfortable. But when it comes to relationships, I do seek secure relationships that are clearly defined. I know I should relax and open myself up to vulnerability, so I can learn to enjoy dating more in the future.

Additional comments?
Tim insisted on being a gentleman and paying for dinner, which was very sweet of him, but I want to get the next one.

Day One   /   lettering by ROANNE ADAMS / RoAndCo

Timothy Goodman

Did you see Jessica today?

What did y’all do together?
We both teach Wednesday nights, so we went out to dinner after class to the Fat Raddish. Jessie brought me a little care package of stuff to jokingly get me through the next 40 days. (And she remembered that I like Clif Bars!)


Did anything interesting happen?
When we set the date for this project, I didn’t realize it was actually the first day of spring. I feel like it’s some sort of omen for us. Anyway, dinner tonight was pretty normal, not unlike other times we’ve hung out and had dinner.


Did you learn anything new about Jessica?
We talked about our families more than we ever did before. I didn’t know that her parents grew up poor. It was refreshing to hear this since I didn’t grow up with a lot of money, either.

Did you learn anything new about yourself?
Earlier in the day I sent a little note to Jessie by messenger. I wanted to honor our project together with something lighthearted.

How do you feel about this relationship/project right now?
The new Justin Timberlake album came out yesterday and it’s totally got me in the mood … But really, Jessie and I should share a “JT” logo with him. Anyway, I feel like there was definitely a moment last night when we both said to ourselves, “Damn, are we actually doing this?!”


Is there anything that you want to do differently?
No, not yet. I did insist that I pay for dinner since it was technically our first “date.”

Additional comments?
I went out with a girl last night, as sort of a ‘swan song’ for my single-hood. Well, she and I ended up talking about the Forty Days of Dating project the entire time. Not exactly what I was anticipating. She was very excited. She thinks Jessie and I are going to fall in love. She texted me later that night: