Thanks so much for the compliments! I’m flattered beyond words. Here go some answers!
Q:How did you come up with this?
A: I was itching to make a web series of my own. I thought long and hard about myself, and what makes me who I am. What are some of my strong points of view? What do I care about? What makes me happy or sad or angry or annoyed? What makes me unique? There could’ve been many answers but something stuck out in my head. The idea of being dumped and alone. I had strong memories of a previous time in my life when things felt different. In my memory this time frame had a very cloudy, gray, lonely, vibe. I thought that’s it. I always get super sad when I’m single. I’ve almost only been dumped in my life, Romantically, I’ve got some abandonment issues. So just stuck in my head, “I Hate Being Single”. And the name would sum up the show. My favorite tv of my life has been sitcoms, from a young age it was 80/90s sitcoms, then older it became stuff like the Freaks and Geeks, UK Office, Curb Your Enthusiasm, etc. So I thought about how it would look and feel and that it’d be a combination of everything I liked. Most importantly I wanted to be honest in the situations and the point of view of the characters and keep it relatively grounded throughout.
Q: What was the writing process like and how close to your real life did you get?
A: I usually wrote episodes 1 at a time. I’d start with a bunch of ideas that were loose premises on a notecard. “Rob puts on a snuggie during a date” “Rob becomes friends with his banker”. Then I had cards that were loose ideas like, “brunch is too expensive” or “everyone thinks rob is cheap”. Then I organize and pick the ideas from the pile and see what could be strung together into an episode. Start with the big idea, the main climactic scene, and then add smaller ideas throughout leading up to it.
A lot of the ideas come from real life for example: Being dumped, befriending my banker, friends talking about hipsters to me when I think they secretly mean they think I suck too, bringing food to brunch, feeling out of place at a small get together, having a “check in date” that leads to more rejection, having friends but still feeling alone, feeling pressure to be/act cooler than I am.
Then there’s things that weren’t real life but come are inspired by anyway. In real life I do own the home-made snuggie, my girlfriend has one too, we wear them all the time at home, all winter long, together. I thought, “If I was single, this is what I’d want, to wear a snuggie with a girl.” So fictional Rob cluelessly gets his snuggie on thinking it’ll be fun and cute but it’s not because it’s a first date, OR because this girl is not that type of girl.

Q:Any general tips?
This comes with the same lessons from above. From my experience, what’s worked for me is being honest. I can’t take credit for the advice I’ve heard the same from the big guys like Apatow, Feig, Shandling, and many other sitcom writing books at barnes and noble. If you follow things in your life that are true, start with that. Watch your favorite shows and think about where you want to draw inspiration from. If you collect many pieces from different places and mix it with your personal experience, the outcome will be something new.
Another big tip is:
DON’T GIVE UP!
Making a series is hard hard hard work. It requires a lot of patience, perseverance, and bravery. I wrote a lot of things and immediately thought, people aren’t going to get this, or “they’re going to think this is dumb, or boring or there’s not enough balls jokes, and there were many times I thought this is just too hard, I’m too tired, I have no money, I’m bugging people to do this project and I must be a selfish psychopath to make a show starring myself. You might hit those same negative thoughts but don’t give up. There’s nothing better than following through. People really appreciate it if you have a vision and want to see it through. I wouldn’t have believed it until it happened first hand but It’s literally changed my life for the better. I’m lucky in the present to have a girlfriend and some close friends majorly supported me and made sure I kept it going. It takes a lot of help from other people so be good and show them it was worth it. What do you think about when you’re about to sleep, or you just woke up? Those daydreams where you see yourself in a show or a movie? Write it. That’s probably the deep stuff. Trust your gut.

Thanks for asking questions and for watching. I hope this helps. Keep me posted on the show!