You’ve been with your current boyfriend for just over a year, and although you do love him, times have been rough recently. He’s been going through a difficult period after an unexpected loss in his family that’s really taken a toll on your relationship. You’re actually relieved to have some time to yourself when he heads to Vegas for a guys' weekend.
You're completely shocked when you get a phone call in the middle of the night from your boyfriend — he’s calling collect from jail. It turns out that he and his friends decided it would be fun to sneak into one of the nicer hotel pools after hours and steal drinks from the bar. You’re completely shocked at his immaturity, but he’s begging you to help bail him out. He sounds really upset, but then again, so are you. How would you handle this?