This question comes from Gerald in Washington, DC.  He writes,

QUESTION:  Love the column, Trey.  I have a friend who started dating a guy a few months ago.  She wants things to progress but he has certain “quirks” that are holding them back.  For example, but he says he is a sharpshooter for the government.  He also lives in a different city, but when she goes to visit him, he insists they stay in a hotel.  In fact, the last time they were there, the police followed them from the hotel to a restaurant and pulled him aside.  Apparently he had a $2,300 tab from a prior “incident” at that hotel.  She paid it because “she did not want to see a brother go to jail.”

I am trying not to judge because I want her to be happy and she always says I am too critical of her.  Do you think I should tell her that I have lost count of the red flags (“sharpshooter,” “insistence on hotels,” “unspecified incidents”)?  If so, how do I break it to her without tripping over her sensitivity?

TREY SAY:  Gerald, since you don’t want to “trip over her sensitivity,” allow me to do the dirty work for you:  Your friend is an idiot.  So let me get this straight; your friend is dating a sharpshooting, government man of mystery that likes to stay at hotels, and racks up unpaid bills at said hotels?  Not only that, she was willing to drop two stacks because “she did not want to see a brother go to jail”??  Please.  She should have sent him to prison and have his ass get sold for two packs of smokes.

Let me categorically state that women are smarter than men when it comes to pretty much anything exceptfor relationships.  I can’t count how many women I know that make all types of excuses for their cheating, lying, deadbeat men because of “love,” and obviously your friend is no exception.  Any logical person would know that this dude is married and probably works the late shift at Arby’s.

Just to prove that I’m right, you should take a trip to the city this dude lives in and pretend that you’re a college student that is writing your thesis on goverment sharpshooters, and you’d like to meet him for coffee.  Have your friend set it up.  If he waffles on the meeting, it’s probably because he’s too busy cooking waffles at IHOP, thus being a fraud.  In any case, impersonating a government official is a felony the last time I checked, so tell your friend to run – not walk – away from this dude.