Cover art for podcast What She's Thinking: men's dating & sex questions answered by women

What She's Thinking: men's dating & sex questions answered by women

35 EpisodesProduced by Greg Schwartz, Debug DatingWebsite

Men, submit your dating + sex questions to have them answered by female guests, moderated by your dating coach Greg


Building CoupleUp Dating: good things but a bit depressed

CoupleUp has soft launched in the San Francisco Bay Area, so if you're nearby go sign up at! Continuing to share updates as I build. 

Want to come on the show when I resume Q&A with ladies? Email greg AT debugdating DOT com


Here's what I talk about in the episode:

Last week was challenging.

I'm feeling a bit depressed today; definitely was yesterday as well. And there's some good things, so I want to share those, too.

Since I've mentioned before that I struggled with depression, I want to talk about that. Not just pretend everything's amazing. My counselor frequently reminds me to not just focus on the negatives, as I have a tendency to do.

👍 Last week we hosted a workshop with awesome dating therapist Jessica Engle. She came in and taught some great stuff to make video dating a better experience. I wanted to highlight her video inside the app, ala Zoom. (In the app there's a big video feed up at the top -- usually me. Then there's smaller video feeds of other people within the speed dating room.)

👎 Spent the entire week on highlighting video. Was still buggy in the workshop.

👎From what people have told me, they could only see me, Jessica, and 2-3 participants.

👍We actually sold out of tickets for the workshop!


👍 Three people have reached out to essentially say "CoupleUp sounds amazing. I want to see it happen. How can I help?" This is especially amazing because I frequently feel *very* alone. Not just in building CoupleUp. It's a long-time thought pattern -- I'm always the outsider; always different from everyone else. So it feels really good to people wanting to be on my team.


👍 From the first speed dating event, we had 1 match.

👍 From the workshop, we had 2 matches! Mind you, is that as good as I'd like? No! But, I'm looking on the bright side, so that's something else to celebrate.

👍 That's a thing that I've learned. I need to celebrate wins, even small ones.


👎 Had to cancel the speed dating on Sunday because of some technical issues -- again, frustrating.


So this week is mostly going to be getting more people on the app. I'm going to expand outside of people in their 30's! If you're reading this, it would be super helpful to keep sharing about the app with your single friends. 🚀🚀🚀

👍 Moving to an *even more* progressive registration flow. (excuse me while I nerd out on design) It won't ask you your name until you're signing up for a speed dating event, plus other changes to get you into the app faster.

👍 I have a counseling appointment on Wednesday. That'll help.


❓ Would you rather use a supportive singles community on Slack, Discord, or Facebook❓ Eventually it'll be in the app, but I don't think that's the right spot for now. (Though I'm open to being convinced otherwise!) Going to do a focus group on that soon.

Last thing: It's not the easiest update to share, but it's important to me to share that building a company isn't always "everything is awesome!" I suspect these are going to stay bi-weekly instead of weekly; that seems to be the cadence I'm hitting. Thank you for your support!


CoupleUp is on Facebook and Twitter, follow on the journey!



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