He asked me out on a date last night to XS, a trendy Baltimore restaurant that serves sushi, coffee and cocktails and has a DJ spinning every night.
The food was great and the atmosphere stellar but I doubt “Douglas” will go anywhere except straight into my friendship file.
During the date he went on and on about all the courses he was taking to improve himself, all the clubs and activities he was involved in, and how he was planning on taking a shopping trip to New York City the next day to get some new clothes.
“What’s your birthday Douglas?,” I asked nonchalantly.
“Oh, a Capricorn.”
“Yeah, right. That’s nice that you know.”
But all I was thinking to myself was, “Yeah, typical Capricorn trying to impress me with his social status and success stories. Boring. Can’t he talk about something other than himself? Or at least flirt a little.”
Now that I’m dating again I’ve learned to weave questions into conversations to figure out whether the dude will be a friend, a potential fuck buddy, a possible new relationship, or someone to kick to the curb. These questions include checking out their astrological sign (read my guide about that).
Or I listen for cues in their conversation that may hint the motherfucker is crazy.
Here are a few questions I ask and conversation points I note:
— How many serious relationships have you been in in the last five years? (If it is three or more this person is probably not good relationship material. Or they are people who rush into relationships without getting to know the person well, something I and a lot of other folks are guilty of)
— What kind of relationship do you have with your parents and family? (If a person doesn’t have a good relationship with the family could be a bad sign that there is unresolved family drama that could affect how they view a relationship. Conversely a person that is always has to care for a family member or spends a lot of time with family may not have time to really date).
— Are you out or not out? (Everyone’s comfort level with being out is different. Some are out to family and friends while others are not out at work. Differences in how out you are can have a huge impact on friendships and relationships. I remember spoiling an evening boat trip with my ex Morgan because a couple was onboard that knew my ex-wife and did not know I am now gay)
— Were you sexually abused? (Unresolved sexual and emotional abuse issues could have an impact on how this person treats relationships).
— You smoke weed? How often? Wow, you have had three drinks in an hour. Do you usually throw them back like that? (A little drug use or alcohol use may not be a big deal. But if the person has to smoke weed several times a week or use drugs or alcohol to get in the mood for sex or enjoy themselves then we’ve got a problem).
— You are a little short on cash and want me to cover the tab? (Dude is broke or is a poor money manager. This is a big, fat red flag. Run, don’t walk, away from this brother.)
— Wow, that is a nice messenger bag you have. It’s Coach. Wow, that must have cost a few hundred dollars. And you say you are renting and have two roommates? (adult men who wear trendy clothes but don’t own a window or a pot of piss to throw out of it may not make good dating choices.
— You hate your job? Wow, that’s too bad. Maybe it’s time for a change (People who hate their job but just go in to get a paycheck may not be the type of person you want to roll with. I believe a man should have passion and enthusiasm about what he does and should be ready to change jobs if the shit isn’t pleasing him.
— You really think Beyoncé is the best entertainer around? What makes you say that? (This person has a limited musical taste)
— Are you into one-on-one sex, threesomes? You ever been to a sex party? (Hey, to be honest I like sexually liberated people. It’s best to get that out very early in the dating process. There is nothing I hate more than guys who say they don’t get out that much sexually but really do. I respect honesty about sexual needs and wants)
— Okay are you a top, bottom or what? (Yeah, this question should have been settled before you went out on a date but some guys keep this a mystery for some reason)
— Where do you see yourself in five years? (Does this dude have plans. Even if it is likely his fantasy will never become reality it’s nice to with people who have dreams and aspirations).
Q: Readers, what are some of things you ask people you date to feel them out?