Dr. Date: My ex-girlfriend just asked me to bail her and her new boyfriend out of jail

The worst part? I actually did it…


by Dr. Date

Dear Dr. Date, 

My ex-girlfriend and I were together for two years in high school — a lifetime in teenage relationships. We broke up a few months ago (after trying the long distance thing at different colleges) with no hard feelings, until I saw her making out with someone on her Snapchat story the very next day. Come on, at least give me some mourning period…

Anyway, we’re not exactly on the best of terms, which is why I was super surprised to get a call from an unknown number last week that turned out to be her — asking me to bail her and her new boyfriend out of jail. I balked and hung up, but not before telling her that her next boyfriend can deal with it. I thought I was being cool and assertive … until I felt bad, went down to the courthouse and bailed them both out. Two years is a long time, okay?

Now I’m not sure what to do. She broke up with her new boyfriend because of the jail thing, paid me back for bail and now is talking about getting back together. What am I supposed to do?!


Locked in my Heart

Dear Locked in my Heart , 

Uhhh … this is a predicament (and yes, I’m annoyed you didn’t mention WHAT she was in jail for. There’s a big difference between stealing a candy bar and assaulting someone!) But no matter what happened that landed her and her boyfriend in jail, I wouldn’t get back together with her. This whole situation is so weird and you deserve someone who A) has friends they can call instead, WTF? and B) wouldn’t do that to you. Tell her you’re not interested and thank your lucky stars you got the bail money back.


Dr. Date