40 Love Lessons From “40 Days Of Dating”

No wonder Hollywood is clamoring for the “40 Days of Dating” project to be the next big rom com or TV series, it has been our addictive, lunchtime reading of choice for the last month and a half. We’ve become maybe a little too invested in following the blog entries of hopeless romantic Jessica Walsh and self-professed commitment-phone Timothy Goodman as they embarked on their 40 days as a couple. How invested is too invested? Well, let’s just say that Ami had a dream that she was out on a date with Tim and he ran away and abandoned her while she was peeing. Sure, it was a dream, but it somehow seems like perfect metaphor for Tim and Jessie.

As women who were both on the NYC dating scene for a long time, we related to Jessie and often saw so much of ourselves in her that it was painful to read. We wanted to shake her and tell her that she would never find what she was looking for in that guy. And as for Tim? Been there, done that. We’d dated “him” so many times that he felt like our very own ex. They’re on day 39 and we’re thinking the outlook is not so good for them. We’re basing this on a quotes from Jessie and Tim’s latest entries:

Jessie: “While we’ve been having a great two days here, Tim finds moments to slip in negative remarks. He said I’d be more attractive to him if I would gain more weight and have more curves.”

Tim: “I don’t want a partner who’s main objective is to be a great mate. I want to be with someone who can be herself, and someone who will let me be me without concern.”

Could they be any more glaringly ill-suited for each other? Their future as a couple non-withstanding, we’ve recapped some of the valuable lessons we learned from the trials and tribulations of Jessie and Tim.

1. When something scares you, it’s probably worth trying.

2. Therapy can be a good thing for a couple — but only if both parties are equally committed to getting something out of it.

3. Guys appreciate it when you trust them enough to share stuff from your past with them — but you need not divulge everything all at once.

4. Everybody has a different communication style. Tim likes to chat a lot over text and IM — Jessica, not so much. This can cause drama if people aren’t clear and up front about what it is they’re asking their partner to do for them, communication-wise.

5. Guys can get defensive about their weird bachelor dude habits, so tread lightly.

6. Trying to see your partner every day can be stressful — make sure that you’re respectful of each other’s schedules and space so that neither one of you feels crowded out or overwhelmed.

7. Be careful that your relationships isn’t ABOUT having a relationship. Sometimes it’s easy to make talking about your relationship the main focus of your time together — like Tim and Jessie do when they have relationship art therapy. It can be really overwhelming and not productive to wallow too much in your feelings.

8. There’s a time and a place to talk about your feelings. That time and place is probably not when you’re out with friends having drinks.

9. Passive aggressive behavior is really, really, annoying. If you have something to say, say it!

10. Beyond that, passive-aggressive energy can literally make you sick.

Day 8: Timothy makes a video for Jessica from 40 Days of Dating on Vimeo.

11. You need to decide whether you’re in love, or if you’re in love with the idea of love. The two are not the same thing but are often mistaken for one another.

12. It’s good to move outside of your comfort zone — to try new things, especially if they’re something your partner really loves. See it as an opportunity to share something special with them that they really are about. In Jessie and Tim’s case, that meant going to a Knicks basketball game — something Jessie would have never done on her own, but which she found herself enjoying anyway!

13. Try not to take out your crabby mood on your partner — separate what’s bothering you from the person your with. Articulate that you’re having a bad time, so your partner doesn’t take it personally when you seem distant or annoyed.

14. Be honest about your intentions, because people can TELL when you want something more from them and aren’t saying. You AND your partner don’t need the additional stress of reading each other’s subtext.

15. Your friends care about you and want the best for you. But if your friends are getting too involved in the status of your relationship, you need to establish boundaries. There is such a thing as too many cooks in the relationship kitchen.

16. Everyone has elements of themselves that are fundamental to who they are. If you like certainty and your partner loves drama and suspense, you may not be well-suited for each other.

17. Dramatic ultimatums are not a good look.

18. It’s okay to want what you want, even if it’s not something your partner can give you. But that may mean that you’re not with the right person.

19. Don’t confuse “dating someone with commitment issues” with a challenge you can either win or lose. You’re just setting yourself up for failure and heartbreak.

20. Sometimes being physically affectionate can release your weird relationship tension. 

21. The little things can make a huge difference, but don’t put too much stock in them. An anniversary note doesn’t necessarily mean he’s all the way in.

22. If the guy you’re dating is literally giving you crippling headaches, time to pack it up.

23. You can tell a lot about a person by what their exes have (or don’t have) to say about them. Tim’s didn’t have anything to say about him.

24. Lowering your expectations is good, lowering your standards is not.

25. Less of the stress, more of the sex.

26. Actually, having things in common does matter in the long term. That opposites attract stuff is BS if there are no similarities between you.

27. Just because he watched “Sex and the City” doesn’t mean he knows shit about women.

28. Sometimes relationship advice is best given by Grams.

29. Living a healthy lifestyle will have a positive affect on your ability to make clearheaded decisions about your love life.

30. When a guy is much more into dating someone who he knows he doesn’t want to marry, he’s definitely not ready to get married.

31. There is a such thing as not having room for someone in your life, but it’s important to make sure that you aren’t staying “too busy” for love.

32. Intimacy isn’t getting close to someone just because they’re close by.

33. We all have roles that we feel comfortable playing when we’re in a relationship and breaking those patterns are really fucking hard.

34. Holding hands for eight hours straight may make for awkward peeing situations, but it won’t solve any fundamental relationship problems.

35. Little disagreements can ruin a relationship, while hugging it out can save one.

36. If the thought of going on a weekend getaway with the person you’re dating is giving you anxiety, it’a probably too soon.

37. If it looks like daddy issues and smells like daddy issues, it’s daddy issues. Tim is finally making the connection that his “leave them before they leave me” attitude has to do with his father abandoning him.

38. Looking for signs of fate in something like a horoscope will not help you make hard decisions about the future of your relationship.

39. A trip to Disney World won’t make you compatible if you’re not. If he makes negative comments about you at home, he’ll continue to do it at the Magic Kingdom.

40. Don’t be afraid to end things. Whether it’s been 4 dates or 40, if someone’s not right for you, don’t force things.