Jess and Tony invite a group of friends to talk about their experiences with modern dating. Dating has become so hard now a days! Everyone comes to the conclusion that organic dating is far better than online dating but for some reason everyone is online dating. A psychologist joins the group to help everyone better understand why we should organically date and put our swiping to the side.

Tony and Jess with guests George and Lexi talk about how to end a relationship. Tony comes up with a new term, Parachuting Out. After Jess ends her "friendship" with her ex Tony couldn't think of a better word for ending it. When you jump out of plane there's no way to get back in, she gone!

Jess and Tony are back with Season 2! Listen to the first episode of Season 2 “Dating Down” which is when you lower your standards to match with someone at a lower caliber than you. Tony think dating down is mainly about money while Jess thinks there are lots layers of dating down.

Singling made it to 20 episodes! Tony and Jess celebrate their 20th episode reminiscing over their prior episodes. Jess is still Cupcaking boys and Tony still hasn't completed operation kiss. They decide to just embrace single hood because getting dumped sucks! Enjoy the show!

Jess and Tony hit 19 episodes with their newest episode all about Modern Dating. We know Tony doesn’t date so Jess breaks down what it’s like to date in 2017. They discover some pros but mostly cons in Modern Dating from all the new technology to the lack of social skills. You might as well stay single because this game is exhausting!

Do opposites attract each other and if so do they stay together? Jess and Tony discuss if the best relationships are with people with the same commonalities or people who are opposites. Jess and Tony have a special guest Mihir join the conversation with his views on what makes his long term relationship a success.

MILF’s – Bad Moms

Tony thinks it’s a good idea to do an episode on MILF’s with a special guest Miss Erica who is the ultimate bad mom. Erika and Jess bonded over beers at a 5 year old kids birthday party and the rest was history. Listen to Jess and Erika talk about the pros and cons of being hot single moms.

Jess and Tony have a special guest on all the way from Canada, Laura Bilotta from Single in the City! Laura is a dating coach, author and matchmaker. Laura helps Jess through her most recent Breakup and helps gives tips on dating. Not all things end happily ever after but we all know there are plenty of fish in the sea.

Can men and women really be “Just Friends”? With guest Christina, Jess and Tony talk all about being friends with the opposite sex and how that can affect a relationship especially a new one. Sometimes you don’t know what you want until you see that it’s not available anymore.

Is in office dating a good thing or bad thing? Sexual Harassment is a thing so you can’t be going around ass grabbing. Jess and Tony talk about the good and bad in dating at the office and the best way to get out of it. Jess thinks if the relationship goes south you can always just quit your job.