Age Isn’t Always Just a Number When It Comes ...

Navigating dating at any age is hard, but realizing the person you love isn't someone you see a future with? That's a whole different kind of heartbreak. Today our writer is asking at what point do you stay and enjoy the relationship for what it is and when is it time to break up ...  Show more

Happy Monday, friends! You've been here through it all, engagements, weddings, and all of life's ups and downs. This week's episode starts with a wild story about a bridesmaid who gets uninvited from the wedding, and then shifts to something much more personal. Today is a difficu ...  Show more

A typical U.S. couple will have an age gap of 2.3 years -- but this wasn't always the case. Join Caroline and Cristen as they explore the average age gap, May-December relationships and the ultimate question: How large is too large of an age gap?

Age gaps are on tap this week and we're discussing it all — dating older, dating younger, pros and cons, power imbalances, sexual compatibility, and more. We share our (and our listeners') experiences of dating with an age gap and what to look out for if you venture into this typ ...  Show more

How big is TOO big of an age gap in dating?? Dean reveals what happened when he dated an older woman when he was in his early twenties!   Sharing your location with your significant other can be a sensitive subject in a relationship, and we hear about how Dean got caught by Caely ...  Show more

Making and keeping friends as an adult is harder than it looks, especially with long-distance friends. Is texting each other every few weeks enough to maintain a close friendship? Is replying to your friend’s Instagram story an actual interaction or just an easy way to feel like ...  Show more