Day Thirty-Seven   /   lettering by Mikey Burton

Jessica Walsh

Did you see Timothy today?

What did y’all do together?
It was our final therapy session together. While often difficult, I do love the therapy sessions. I think anyone can benefit from therapy, no matter what the reasons or goals. Go with your lover, go with your husband, go with boyfriend, go with your best friend. Take your pet! It’s amazing to shed light onto your day-to-day insights, if only to bring more awareness to your actions and choices.


Did anything interesting happen?
Jocelyn asked us what we wanted to do now that the project was ending. Tim said he really does want to date me exclusively, he just couldn’t give any marriage commitments yet. Wait what? Marriage?! Where did that thought even come from? Still, I agreed that I’d also like to try dating him outside the context of the project.

Jocelyn brought up how Tim was “in control” during the entire experiment. She asked me to analyze why I became so submissive around him. In previous relationships things were much more balanced, or I often had more control. Throughout this experiment and relationship, everything has felt like it is on Tim’s terms. Part of me always feels on guard around him too, as he can be sensitive and I am afraid something I might say might bother him. It’s interesting how we can be (or become) such different people depending on whom we’re with, or on the situation we find ourselves in. No wonder relationships are so difficult. It’s not easy to entirely understand yourself, let alone the person you are with. We are all constantly growing and evolving.

She also challenged me to think about why it was so difficult for me to feel so out of control during the experiment. My own personal therapist has told me that I have major control issues. He says I like to highly control, organize, and curate every aspect of my life as a way to cope with a painful situation from my past which I had no control over. It’s part of why I like things in order, part of why I try to make things appear perfect, and part of why I have avoided meaningless relationships that might leave me vulnerable. He has challenged me numerous times to face this fear by completely letting go and relinquishing all control. I didn’t understand what that meant or how to go about it.


In some strange way, this experiment ended up being the answer to this. We also discussed the importance of me putting less pressure on myself and learning to say “no” more often. When I take on too much, I become miserable, and both my work and relationships suffer. We discussed how much happier I feel and how much my outlook and mood has changed since I’ve started taking better care of myself.

Did you learn anything new about Timothy?
Jocelyn discussed how Tim’s cycle of abandoning women likely goes back to being abandoned by his father. Jocelyn discussed how men will repeat this pattern in a way to identify with or feel closer to the absent parent. Over time, this pattern only makes the person feel emptier, as they never develop meaningful relationships.

Did you learn anything new about yourself?
We talked about how empowering it was for me to “let go” a few weeks ago and to stop trying to define the relationship. In the past I have put too much pressure on myself to determine if the person I was dating was right long-term. If a guy didn’t give himself to me wholeheartedly, I would give up on the relationship out of fear of failure. I couldn’t enjoy dating in the moment.

How do you feel about this relationship/project right now?
Tim mentioned how it would be a tremendous relief to date without the burden of recording everything every day. Amen!

Is there anything that you want to do differently?
I am looking forward to dating Tim outside of the experiment, but I don’t want to accidentally pressure him. There is no need to rush. I want to enjoy the journey, not get hung up on the destination.

Additional comments?
Disney World! Tomorrow!


Day Thirty-Seven   /   lettering by John J. Custer

Timothy Goodman

Did you see Jessica today?

What did y’all do together?
Weekly therapy session. Last call!

Did anything interesting happen?
Jolecyn reinforced that I’m the “dominant” one in this relationship. I seem to be the one who’s in control, because I’ve been on the fence, while Jessie has been willing to dive in head first. I guess by default I am in control, but I don’t understand why Jessie can’t take some control. I’m not holding us for ransom, nor do I want to. I remember reading something a while ago about how relationships don’t fail because of little differences. They fail because of arguments about who is in charge and who is not in charge, and the stress that comes along with that.

We talked a lot about what Jessie and I have learned from the last 37 days. We talked about what we’re going to do after Sunday. Admittedly, I’ve been trying to avoid thinking about this. Jocelyn asked me if I want to go back to dating other women. I have no interest in seeing other women come day 41 or thereafter, and I don’t want to stop seeing Jessie. I just want to see what happens when we’re outside of the parameters of this experiment. This hasn’t been “real” dating, and nothing about this experience has necessarily felt natural. While pressure can create diamonds, sometimes pressure can blow out from the bottom. I’m interested in seeing what could happen when we’re “unchained.”

It makes me think of Dave, a former boss of mine I had right after high school. He eventually became an important mentor and a great friend. He has all these phrases he goes by, stuff like “dress for the job you want, not the job you have” and “never put your hands in your pockets, it’s a sign of laziness.” Anyway, one phrase he says that particularly rings a bell in this case is, “never say ‘I can’t.'” When will I stop saying ‘I can’t’ when it comes to relationships?


Did you learn anything new about Jessica?
Jocelyn brought up how hard it is for me when Jessie gets down about things. That can have a major effect on your significant other, and it’s truly affected me throughout this experience. Jocelyn asked me to describe to Jessie what that feels like to me. Then Jocelyn mentioned to Jessie how valuable it is to hear something like this without the heat of an argument. She said it’s a significant piece of information for Jessie to know as she goes forth.

Did you learn anything new about yourself?
Jocelyn said I abandon women before they abandon me as a reaction to my missing father. This isn’t news to me, obviously, but when someone tells you that to your face it’s like a punch in the gut. I know it is a defense mechanism, a way to “get” them before they “get” me. I’m not proud of it.

How do you feel about this relationship/project right now?
I feel good about it. I feel like Jessie has been consistently chill the last two weeks, and I’ve been consistently allowing her into my life. I don’t feel the pressure from the Gala anymore. I don’t feel pressure from her. I love this.

Is there anything that you want to do differently?
I want us to have the best possible time on our trip. I don’t want to worry about what’s happened in the past, or what could happen in the future.

Additional comments?
I love making playlists for friends, and I love making playlists for trips. There is a real pleasure in carefully and considerately selecting tracks that are appropriate for someone or something. (And I always need a reason to bust out Huey Lewis or a classic 90s alternative song!) Obviously, I had to make a 40DD playlist for this Disney Trip! 40 songs that highlight every moment, smile, tear, or any other related experiences we’ve shared through this experiment.