Jared opens up to Vanessa about a recent Hawaiian vacation with girlfriend Ashley. He spills all the details on the romantic getaway and the compromising position housekeeping caught them in!

Author, Heather Monahan, calls in. She and the gang discuss confidence in dating, and how Vanessa can apply it to her own love life. And Dean still sucks at dating whether he lives in a small town or the big city.    Learn more about your ad-choices at https://news.iheart.com/podcast-advertisers