Hilary goes on her first first-date and finds the goods are not quite what was advertised.

Plus, an oversharing bookseller and the flaky 'poetry guy' test her fragile heart.

How do you deal with people who lie, overshare, or don't respect your feelings? Hilary confronts the reality that the people she meets on the apps might challenge her trust while looking inward at how her baggage affects her interactions. Older daters are covered in scars. Some heartbreaks and hang-ups significantly influence how we connect with others. So, how do we protect ourselves while trying to be vulnerable with strangers?