40 Days of Dating and One Big Asshole


Today marks the last day of the “40 Days of Dating” experiment, a forced courtship blog run by two successful, telegenic graphic designer friends who decided to very publicly try dating each other. Timothy Goodman is the man-child commitment-phobe; Jessica Walsh is the hopeless romantic. Since the duo documented their daily dates, weekly couples’ therapist appointments and 24/7 neuroses, readers can make educated guesses as to why they (spoiler) didn’t work out. Mine: because they’re both insufferable.

Eh, I feel bad calling Jessica insufferable; she’s just not my type of gal. She enjoys running around the city pretending to be Amelie and comes up with analogies like, “Our relationship with Disney World, like each other, was deeply conflicted and complicated. We are so wrong for each other in so many ways, and so right for each other in many other ways.” She bugs me, but seems like a very nice person with great bangs.

But Tim! Tim is such a dick to her. He writes endlessly about how neurotic and complicated Jessica is without realizing that he’s the hopelessly messed-up one. For example, on Day 34 — that’s like a year of intimacy in real dating time — Jessica mentions to him that a girl he briefly dated might be at a party they’re attending. Tim irrationally freaks out and goes into this rant about how Jessica is a devious manic pixie “tricky girl”:

The tricky girl thing is totally my Achilles’ heel. I’m at this kind of girl’s mercy. You can NEVER tell what’s on a tricky girl’s mind. The tricky girl will unknowingly rip your heart out, cut it into little pieces, and then ask you, politely, if she can feed you. I’ve fallen hard for girls like this in the past. I guess I’ve always known this about her, but now that we’re in this relationship, I’m seeing it in a whole different light. Everything that happened tonight was a classic tricky girl situation. I’ve dated girls like this before, and it always drove me nearly mad. And the funny thing is that one man’s tricky girl doesn’t necessarily make her another man’s. Someone else might date Jessie and not see ANY of this. A tricky girl is situational, and circumstantial. It depends on all parties involved. I’m not built for a tricky girl. Oh dear.

But Jessica isn’t tricky at all! She’s always trying to be open and work things out:

After I walked out of the tourist shop, Tim ran after me and grabbed my arm. We sat down in the grass together. I asked him to think hard about what he was doing. Was he doing this as his usual defense mechanism? Is this his fear of vulnerablity? If so, I was willing to work through it with him. On the other hand, I’ve been completely open and honest with him about who I am, and what I can offer him. If he doesn’t think we are working romantically, then we should end this now and try to remain friends.

In the meantime, Tim’s stuck in his own head, wishing Jessica would make him do things he insists he doesn’t want to do, like he’s a little baby. Which he is.

Selfishly, part of me wishes that she could be more of an aggressor, someone who would try to convince me to change my mind once. I know it’s not her style, but, selfishly, I wish her actions showed it as much as her words. Maybe she gives up too quickly. Maybe I want someone who’s gonna fight for me. Maybe that’s all BS, and I’m just making cowardly excuses. Maybe she just loves love. Maybe I’m just a scared little boy who can’t man up. Whatever it is, I know she deserves more. She doesn’t deserve someone who is unsure about her.

I mean, if you want to talk about tricky, here’s how he signs off:

As the cab driver pulled up to my apartment, we laughed because it was literally 11:57 PM as day 41 was approaching. I just can’t believe it’s over. I feel so close to her. I know now that I’m in love with her. I love her, yet I know there’s nothing else I can do. We kissed. I gave her a gift. We kissed one more time. I shut the cab door, and I walked away.

Oh, and here’s how he feels after they first decide to break up:

We got back and sat in bed together. As we sat there, we started rubbing each other and kissing. I can honestly say I’ve never been more aroused in my life than I was at that moment. I wanted every single part of her, but there was so much guilt. She whispered, “should we have break-up sex?” I didn’t answer her, and we slowly stopped kissing. Ten minutes later we were asleep.

Here’s my takeaway: never take anything personally — it clearly didn’t work out between these two because Tim is a jerk, not because of anything Jessica could’ve salvaged — and never date this dude. Although they both signed with talent agency CAA, so maybe “didn’t work out” is a misnomer.

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