May 5, 2013: I was talking to my married buddy today. He thinks I’m an idiot for letting Jessie go, but I can’t force something that doesn’t feel right in my heart. He was being like those people who judge a person based only on externals, who say a beautiful celebrity is “amazing” or a “dream girl,” but they don’t know them. That person has no idea how they’d vibe with someone like Angelina Jolie, or if she’s a raging psycho in real life or not. Some people just assume that if it looks good on paper everything should work out. While my buddy is a great guy, with great advice, he’s still unhappily married, and I need to remember to take what he says with a grain of salt. I like this funny quote: “Never trust a married guy’s taste in women. It’s like asking a starving guy what food tastes good.” Anyway, I’m still not sure about my decision to let Jessie go, and even though a good part of me knows that we’re better as friends, I can’t deny that I do miss her.
May 11, 2013: Today was the first time Jessie and I have seen each other since Day Forty of the project. We met to brainstorm and go through the journals we’d kept during the forty days. While we were talking, her phone began to buzz. I looked at the phone, and what did I see? A notification of an OkCupid message! Ha! Wow, it’s been only a week and a half, and she’s already back at it. I knew that’s how it would be. Jessie doesn’t play around—she goes right into reactionary mode. I gotta let it go and not worry about it. Toward the end of our meeting we were hugging and talking about giving it another chance between us. Honestly, knowing that she can run on to the next thing so quickly is a problem for me. It’s clearly my issue more than hers. Anyway, we said that we missed each other, and we hugged for a while. I wanted to kiss her, but I didn’t. I knew that would make everything way more confusing. She gave me a kind of ultimatum, that we should either be friends and not talk about this stuff any longer, or we should date and give it a chance. I told her I thought it was best to stay friends. Okay, I said that, but why do I still feel so confused?
June 5, 2013: There is a lot of work to be done, still, in the creation of the 40 Days website, putting the writing and photos together, editing videos, and making the illustrations. That, coupled with an enormous amount of client work I currently have, has been stressing me out lately. I know I don’t handle it well sometimes. Also, I’m noticing how different Jessie and I can be in the way we approach work. Sometimes we don’t know how to navigate each other. I feel like Jessie keeps giving me a hard time about when we’re going to launch this. I can get impatient, but Jessie can, too. She wants to launch it now, but we really need more time to craft everything. I feel a lot of pressure from her. Then, she’ll apologize for everything, completely change her tone, and become super accommodating—as if nothing has happened. I know she is just trying to be nice, but I get annoyed by the way she switches tones so quickly. I need more time to process everything. But then we begin to argue again. It’s been pretty stressful. I hope we can sort it out.
June 10, 2013: It’s been a month and a half since the experiment ended, and I’ve had no desire to resort back to my old dating ways. Recently I went on a date with a girl who my buddy set me up with. She was the first woman I’ve seen since Jessie, and she was the exact opposite of her: We ate doughnuts, drank beer, and watched the NBA finals. These are things Jessie would never be interested in, so I think I was immediately smitten by it all. We ended up sleeping together that night, and I realize how the whole thing was just some sort of rebound for me. I felt weird about it, but I tried to hang out again two nights later just to make sure. She even made me two bags of cookies, one with a San Antonio Spurs logo and the other with a Miami Heat logo, since these were the two teams playing in the NBA Finals. We had a lot of fun, and I liked her, but I knew it was a mistake. I went out with one other girl who kept saying, “Do the damn thing!” all night during dinner. Seriously? Really, eight times in one night?! I sent her home in a cab.
June 15, 2013: Jessie and I hung out with some mutual friends last night at a cocktail party. As much as I’ve been trying to deny the feelings I have for Jessie, I still keep questioning myself and wavering. I’m obviously still attracted to her, and there’s so much we have in common. Also, having a great friendship as a foundation is such an important part of any relationship. Being back in the dating game hasn’t helped, either. All that careless fun I like to have has been utterly disappointing. I’d really love to find someone special. Gosh, I haven’t had that thought in years, while I’ve been happily coasting from one date to the next. Now I can’t help but wonder: Did I make a mistake? Am I seeing things more clearly now that we’re unburdened by the parameters of the experiment? Or am I simply more interested because she’s recently gone on a couple dates with some new guy? Jessie has stopped taking the sleeping pills she was taking during the experiment, and she seems so much happier and balanced now. This has undoubtedly changed my outlook on the possibility of us, too. Anyway, we shared a cab home from the party, and she ended up telling me that she thinks that I’m crazy but that she still finds me “weirdly attractive.” Well, guess what, Jessie? I think you’re crazy, and I still find you attractive, too. Then she immediately told me that she shouldn’t be telling me that stuff. I wanted to kiss her on the spot. But I didn’t. I knew that would open a whole bag of worms. Also, I wasn’t sure she’d reciprocate, and I didn’t want to risk that rejection. Oh boy, what a mess!
June 25, 2013: I’ve been wondering what would happen if Jessie and I dated in real life. We’ve been arguing more and more about trivial things, but my birthday was two days ago, and she sent me a really sweet email.
I still have major concerns about anything long-term between us, but now that the dust has settled from the experiment, I have some perspective. Everything felt so difficult during the forty days, like a slippery frog that I couldn’t quite catch. Also, Jessie is no longer taking those pills, which makes her a completely different person. So last week, late at night while I was enjoying some whiskey, Jessie and I were chatting on email. I told her everything I had been feeling, and I asked her what she thought about the idea of giving it another chance between us. Well, she wasn’t exactly keen on the idea. She told me that this is just a chase to me, that I’m only doing it because she’s moved on and has started seeing someone new. There is some truth to this: The fact that she’s seeing a guy makes me feel more pressure to make up my mind. I’m not saying this is fair, but the experiment was so hard, and I’m just curious about how we would be together without that self-imposed experiment forcing us to be together. Now, since I told her this stuff, I’ve noticed that we’ve been arguing about everything: about when to launch the project, about what we’ve written about each other, and other things. I don’t understand this; we have worked so well together for so long. But now, even when we’re not openly fighting, there’s this tension and a passive-aggressive vibe between us. At least I won’t regret not telling her how I felt.
July 3, 2013: I’m in New Orleans vacationing with my brother, eating good food, and listening to the best jazz I’ve heard in my life. I haven’t talked to Jessie in over a week. She’s been kind of coy with me. Even though it’s only been a month, I know she’s getting serious with this new guy Zak. I called her from New Orleans, and we had a nice heart-to-heart. She told me she went to Mexico with him on their third date last week! WOW. I can’t help but think how impulsive she is, at least compared to me. One relationship doesn’t work, and she’s on to the next one so quickly. Which, at the same time, is what’s special about her: Jessie doesn’t play around, she knows what she wants. This reminds me of a quote in the film Blue Valentine when Ryan Gosling’s character, Dean, says, “I feel like men are more romantic than women. When we get married we marry, like, one girl, ’cause we’re resistant the whole way until we meet one girl and we think I’d be an idiot if I didn’t marry this girl because she’s so great. But it seems like girls get to a place where they just kinda pick the best option . . . ‘Oh, he’s got a good job.’ I mean, they spend t
heir whole life looking for Prince Charming and then they marry the guy who’s got a good job and is gonna stick around.” I wonder, is this what Jessie’s doing? Only Jessie can know what’s right for her. Despite my love for her, this is one of the reasons I had a hard time imagining us together. I really wish her the best with Zak. I just don’t want her to get hurt, that’s all. Now back to my jazz. According to Miles Davis, “Sometimes you have to play a long time to be able to play like yourself.”
July 9, 2013: Tomorrow we’re launching the 40 Days of Dating website, but today we launched through social media and other venues what we’re calling teaser videos. Essentially, they’re four fun videos we made to get people interested and curious about the project. They received an amazing reception, especially the “behind the scenes” video, which was the perfect metaphor:
The two of us are staring at each other, trying to stay focused, while everything around us (sumo wrestlers, emotions, fears, habits, etc.) is trying to distract us from that focus. We worked hard on them and spent a lot of our own money, so it was gratifying. It was nice for a change to do something more artful and abstract that didn’t involve the emotional burden we’ve been carrying through this whole thing. In a way, this project was an endurance test. We got a drink tonight at the Flatiron Lounge to celebrate the launch.
July 13, 2013: My buddy Greg just told me he’s moving in with his girlfriend. He was the last of my good friends who was single, and I’m feeling a bit more sensitive to relationships and my own single status post-experiment, especially because of this project. I still feel the way I did at the end of the forty days—I understand how awesome it is to be in a relationship with someone that you love and connect with. Anyway, now that my buddy is moving on, I feel like I’m getting left behind. It’s like that Kanye West song when he raps, “My friend showed me pictures of his kids, and all I could show him was pictures of my cribs.” Except my line would be more like, “My friend told me he’s moving in with his girlfriend, and all I could say is that I dated a girl on the Internet.” I know, it doesn’t rhyme, but you get the drift.
July 24, 2013: Tonight Jessie and I got into a heated text message conversation about our relationship and what happened at the end of the experiment back in April. I don’t even know how this happened, but I ended up telling her that I felt like I loved her at the end of the experiment. Since we’ve only posted up to Day Twelve on the blog, she has no idea yet what I wrote on Day Forty. She didn’t seem happy to hear it. We kept going back and forth by text, and I was surprised at how affected she seemed to be by the news. I realize she’s in this other relationship now, but why would telling her that I loved her three months ago, at the end of the experiment, affect her right now? Anyway, I do feel like Jessie and I have unfinished business. We (or I, at least) haven’t yet found closure. I wonder if this is healthy for us—time has moved so quickly, and we shifted gears into creative mode right after the experiment. We still haven’t had enough space or time away to reflect on it all, which has been difficult for me. It’s a funny thing, because as open as I am, I find it difficult to truly open up to someone once I know them. Maybe that’s why I didn’t tell Jessie my feelings at the end? I can easily tell my entire life to a stranger or share my feelings with friends, but once I let someone into my life romantically, I find that I put up walls. For instance, I’ve had no problem talking about my absent father or a painful breakup or a childhood experience to a group of strangers, or on the 40 Days website, but it’s difficult for me to talk about these things one-on-one with someone I care about and who actually cares about me. Mainly because I don’t think the other person can truly relate, and also because I don’t want their sympathy. Then, later, I second-guess myself.
July 29, 2013: Earlier today, Jessie told me she’s quitting the whole thing, and then she told me to “fuck off” by text. This was really surprising, because she’s normally calm and level-headed about these things. Things have been getting worse between us. Jessie is crazy busy at work, and lately I feel like I’m taking most of these calls with agents and setting up meetings for us. So I try to hold it in because I don’t want to add to the drama, but then it just comes out indirectly and we get into a big fight. Last week, we got into an argument, and we both hung up on each other at different times. There are just so many layers and misunderstandings between us, blurred lines, decisions to make, hurt feelings. Now there’s a new kind of pressure because we’ve been getting more and more publicity. When pressure builds, sometimes Jessie shuts down while I do the exact opposite—I go into full-blown annoying soldier mode.
Not only have we been doing interviews all day with the press and taking phone calls from Hollywood film studios and agents, but we’re still doing a lot of work (illustrations, etc.) on the daily posts that requires a lot of time. Not to mention, we’re both trying to manage all of this in addition to our regular work. We’re trying our best, but it’s not working out well. I also think a lot of this is connected to the “love” stuff I told her earlier in the week. I should have kept my mouth shut! But she would have found out anyway.
August 5, 2013: So I’ve been regularly hanging with this great girl for the last five weeks, and I totally blew it with her last night. She asked me to come to an event with her, and I completely forgot about it. I’ve been so busy trying to juggle everything that’s happening with 40 Days of Dating and my design clients that I’ve literally been working nonstop. I woke in the morning to see a text message that she sent around 3:00 A.M. In so many words, she said it was over. Sigh. I feel awful. We had a lot of fun together. She has been super cool with this project, too, considering she’s reading all about me on the blog at the same time as she’s getting to know me in person. A part of me wants to fight for her, but I just don’t want to make promises that I can’t keep right now.
August 10, 2013: Since that relationship ended, I’ve been feeling rebellious and disappointed by the idea of relationships in general. And on top of it all, it’s insane how many women have been reaching out to me. I never expected this—I thought my dating life would be over because of this project—but random women are coming out of the woodwork, emailing, Facebook messaging, Instagramming me notes, and tweeting at me. On the one hand, I don’t know if I have the strength to stay away from these requests. I can’t deny that it feels good, that it boosts my ego. I mean, this doesn’t happen every day. On the other hand, it’s kind of creepy. They all think they know me. I’m constantly worried that I’m getting catfished.
Haley
Hey would you wanna get a drink sometime?
Michelle
You like flirting, i like flirting...so we should be flirting with each other.
Sarah
If you don’t end up with Jessie, can I have a shot?
Raiza
Hi Tim, do you ever find yourself coming out to San Francisco? Let’s hang out :)
Andriana
I wouldn’t mind dating you for 40 days ;)
Nina
If you want, I’m grabbing a drink with a friend in the East Village. Join us!
Alsa
You were in my dream last night...
Rene
Come to London so I can feed you Japanese whiskey and flirt with you.
Some have even found my phone number, and total strangers are texting me in the middle of the night. Do they think they can change me?
Anyway, we’ve been going out to LA and meeting with agents who want to represent us, and we finally decided on Creative Artists Agency and signed with them today. I was feeling celebratory, and I love LA, so I wanted to have some fun. A woman who lives out in LA had gotten in touch with me through Facebook last week. I found her very sexy. So I told her I was in town and asked her if she wanted to hang out. She met me in my hotel lobby that night, we had a few drinks on the roof bar, and she came back to my room. I remember lying in bed with her later in the night, and I asked her why she’s single. She said, “All the guys are either my age and they’re no
t very serious about life, or they’re your age and they’re not very serious about me.” That made me sad.
August 12, 2013: We’re coming back from LA today, and I’m not happy about some recent arguments with Jessie. One big reason we were out there was to meet with this production studio. I know she greatly cares about this project, but all Jessie could talk about was meeting up with Zak. I mean, she was even talking to our lawyer about it. I was annoyed, and I guess I was being kind of an asshole about it, but I was disappointed. After our meeting, she wanted to go straight to see Zak, but I wanted her to have drinks with me and the rest of the team. I didn’t think it was a big deal to hang out with them for a couple hours—that’s why we were there—but she seemed to feel I was being controlling. I get it, she’s in love, but she will have all weekend to see her boyfriend! Thankfully, she joined us for drinks. I think Jessie believes I have a problem with her relationship, but all I want is for her to be focused on the project with me.
August 15, 2013: I’m feeling dizzy! The past week has been insane with interviews and meetings: CNN, Elle magazine, London Times, Fast Company, Time magazine, talk show requests, and meetings with Hollywood studios, producers, and actresses about selling the film or TV rights. All of a sudden our project is “intellectual property.” I literally can’t believe my calendar, and our 40 Days of Dating email inbox is jaw-dropping. All from this little idea? Insane and very humbling. We met a photographer at Washington Square Park for Elle magazine recently, and we got stopped about seven times by people who were fans of the project. One young girl told us that she had had cancer (and beat it!) recently, and after battling depression, she built up the courage to pursue her dreams after reading our story. It was so touching and overwhelming to hear that. The more this project has grown, however, the less control I feel I have. I wonder if all this attention (both from fans and the media) is screwing with my pysche? Here’s what I know: When you win an award for a design project, people will recognize your work. It’s a very different thing when you present your own life on the Internet and are recognized by people outside of your work. For good or bad, people seem to think we’re two-dimensional characters in a movie. Now we’re just riding the wave and trying to juggle everything that comes along with that. I couldn’t imagine being a celebrity. Your anonymity is taken away from you and everyone wants to know you and be with you and have a piece of you. No wonder so many famous people are crazy pompous asses.
40 Days of Dating: An Experiment Page 20