This Week In Web Videos: ‘How To NOT Win Back Your Ex’

Person is born. Person is made somewhat insecure by the travails of daily life and, for some reason, feels a little better when people laugh at him. Person decides to become a comedian. That’s the first half of the life cycle for 99 percent of people who decide to pursue a career in comedy. The other half is the part that determines whether those people will die cold and alone (i.e. be successful) or whether they’ll go on to be happy (oof, tough break). To achieve success, a person needs to bare the deepest excesses of his soul, turning the painful into the true and the true into funny. Being insecure and wanting people to laugh at you gets you up to the mic, but what you say and how that’s received all depends on how far you’re willing to dig and how personal you’re willing to get once you start speaking into it. How To NOT Win Back Your Ex creator Dan Siegel knows that and along with Sam Jacobson, Sam Sparks, Caralyn Stone, Max Goldberg, and a host of other very talented folks, he’s put together one hell of a web series.

How did you get started in comedy? 

I first got started in comedy my freshman year of college. I wrote for this sketch comedy group at my school called NSTV – Northwestern Sketch Television, so it really wasn’t until college that I became a big comedy nerd. I was in the sketch group for three years and then did other shows.

How did you come to work at CollegeHumor? 

After I graduated I moved to New York and I knew I wanted to keep doing stand up and making funny videos so I applied for a production internship with CollegeHumor and I got that and was an intern and then I ended up, very strangely, getting hired to be an assistant production accountant. I got kind of lucky because the production accountant at the time, I think her computer crashed and she lost a lot of data and I was there and out of school so I was able to help out with that, and that’s how I ended up at CollegeHumor. I was freelance as a production accountant for like 8 months or so and then I became full time doing that and then eventually I was able to get back into production and then I became a production coordinator for their sister site, Jest.

What was the inspiration for this series specifically? 

I went through a break up back in April; I got dumped on April 2nd, the day after April Fools Day. It was a real low point and I was feeling very bummed about it, like I had lost my soul mate. So I wanted to write something about it, because it was all I was thinking about. I’m sure people can relate to having really stupid ideas of how to get someone back after a break up. Like how is my brain coming up with these absolutely delusional ideas? And I made a tutorial video of how not to do them. I made the video a few days after I got dumped and it was therapeutic because I was so excited that I had made this web series and even though I was still hurting I was feeling good that I had something to show.

It feels super real. 

Well it’s funny, when I first came up with the idea it was actually too real, so I pitched the idea to my friend, Sam Jacobson and he thought it was really funny and he came on board to co-write it with me. He helped broaden the humor a little bit so that it wasn’t so specific to my situation. It was really helpful to have him work with me. It was such a weird idea, an anti-How To video, it was hard to wrap my head around it, and so it was helpful to have Sam around to help me with it.

It definitely worked. Is this your first web series? You’ve got some serious views. 

No, the first one was this web series for Channel 101 called Sebi & Dani, and also Dan that I did with my roommate who I’ve known since middle school. We did 7 episodes of that. As far as the views for this new web series, I’ve been lucky enough that CollegeHumor uploads them and features them, so once the videos were posted there the view count went up. Also people are always looking for dating and relationship advice and then happen to stumble upon this series.

Had you not had CollegeHumor helping you, how would you have promoted? 

I definitely think it’s good to try and get a big site with a big following like CollegeHumor. If I hadn’t heard back from them I probably would have submitted it to another comedy site like Above Average, but obviously I work for CollegeHumor so I’d be foolish not to use them. My main advice would be “You have to put yourself out there.” I sent out a lot of email for this series, some people responded to those emails, some didn’t. Use social media to plug it. When the series’ first premiered, a lot of the people who were working on it were promoting it. I was very lucky that I had all these talented friends working on this who work for CollegeHumor and they all got involved in this project. Everyone related to this concept and everyone felt like they were creatively involved in this process. They were proud of it, so they wanted to share.

That’s cool. I think some creators aren’t really willing to give out that kind of creative control. 

For me, one of the reasons I like doing comedy so much is that I like riffing with my friends and shooting the shit and that’s what we did with this series. Even the sound mixer was throwing in ideas; everyone was involved in the comedy. I know some people can get very protective over material, but one of the first things I did was reach out to Sam when I got this idea because I wanted to work with other people, I think shows are the best when you have other people coming together creatively.

So what’s next for you in terms of your creative projects? 

I really liked this series, the main character Ian is kind of like my alter ego. He’s like Larry David on Curb; he does all the stuff that I wish I could do. Another thing that I forgot to mention is that a lot of the YouTube comments for this video, they seem to think that this is a real person. Like people saying that this is great that he’s taking this pain and making something positive of it. And I guess that is true, it was a painful thing that I made something positive out of, but I can’t tell how many people think it’s a real person and how many people are in on the joke. I’m interested in making more of these anti-How To videos with Ian as the host. He’s done his break up stories and now he’s going through the anger phase, like “How To Not Get Revenge On Your Ex,” then “How To Not Ask Your Ex For Forgiveness.” I feel like you could just go on and on. I definitely want to do more things with Ian. I also just got settled as the production coordinator out here in LA for CollegeHumor. I have ideas for another project I want to do out here so I’ll start writing that, maybe try and do some stand up, I just need to get my footing down.

And your three reasons to watch.

  • Graphics
  • Honesty
  • Simplicity
  • Episode #1: Memory Collage

    There’s only one way to keep people interested in talking head-style videos for more than 2 minutes. Breasts. Also, amazingly detailed, hilarious visuals like the ones in this series. Okay, so there are two ways.

    Episode #3: Balloon Sculpture

    We’ve all been dumped and we’ve all racked our brain for ways to win the dumper back. How To NOT Win Back Your Ex is relatable on the basest level.

    Episode #4: Web Series

    Siegel wants to make more of these and nothing’s stopping him because this format is very easily repeatable.

    This Week In Web Videos: ‘How To NOT Win Back Your Ex’