Episode 080: Asking out a newly single friend, weird ex-coworkers, & awkward surprise dates

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We are BACK in studio, this time joined with returning guest and my "Capital-R Roommate", Buddy Pearson (@notyorbuddy2)! We kick things off with a quick personal life update, before hearing from some listeners, and answer the following:

• My friend (32F) just got out of a 6 year LTR, how should I (37M) approach asking her out?
• Ex coworker keeps DM’ing and texting me… he has a fiance... Help?
• Weird coffee “date” with old high school crush... What happened?

This is a fun one, so be sure to tune in!