Immanuel’s Gay Dating Interview Questions

Immanuel’s Gay Dating Interview Questions

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.

“January 7.”

“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.”

XS restaurant in Baltimore.
XS restaurant in Baltimore.

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?


  1. PerfectingMeB

    Those questions are interesting. Some would take a few dates before asking and I would say that some answers would differ depending on what you really want. Overall good tips.

  2. I would have to say this was very good advice.Maybe I should start asking better questions. I guess I ask no questions that really reveal the important things , like “Are you crazy?” Perhaps that’s why I have such a horrible track record. I clicked the link to the horoscope guide. Interesting. I see some traits not 100 percent sure if the bad is me or not…I think I like the real horoscope traits mingle and can be hits and miss.

    By the way I read something completely different in the Beyonce question…and musical variety spectrum is not it.

  3. MADAngel

    All very valid questions and I can agree on all points except the job question. In today’s economy, a dude has to do whatever it takes to LEGITIMATELY handle his responsibilities. We’ve all been in situations where bills came first. How many people out here are actually employed in their ideal job. I wouldn’t say many. I don’t think that’s reason to discard anyone. If he’s employed and self sustaining…cool. Of course, I may listen once or twice about how bad the situation is but then that’s it. Step up or step off. lol. The whole horoscope thing I get it but I don’t totally subscribe to it. A friend of mine made a good point; how is it possible for a horoscope (daily included) to apply to every person on this Earth born during that time? I don’t buy it. Each person is an individual and some of those traits may apply but I may be doing myself an injustice to assume. I’m a Pisces, so what does that say about me? I have no lack in ambitions or dreams. I’m deeply engrained in reality. Now in the case of ol boy, he was definitely not dating material. No one wants to hear about you, you you!!!! Especially not on the 1st date. I like to keep some mystery and allow things to come slowly, because they always do. But no real questions to add, Immanuel, just commenting. Interesting blog. Keep up the good work

    1. MADAngel thanks so much for your thoughtful comments. Yeah, I don’t try to overdo the horoscope thing although sometimes it surprises me how accurate they can be. You may want to do your full chart because everyone is in fact a mixture of different signs. You are right about the job situation. What made me write that is the guy I was on the date with is a teacher who HATES teaching. He says he just passes students on to the next grade whether they have the skills or not because he doesn’t want to make waves and besides, kids now have to take achievement tests anyway to graduate. I made up my mind right then not to date this man let alone give him some of this dick. Because any man who doesn’t value black children, especially these days, is not someone I want to call a friend, lover or partner.

  4. PDQ

    I’m now married and have been for years, so I’m not actively looking. But when I was a single Aries on the prowl I was pretty direct and to the point and willing to try just about any damn thing.

    My questions were usually along the lines of:
    1) What are you packin’ ?
    2) What positions / role playing / games / etc. are you into??(bonus points for the freakier stuff – in fact when you wrote that you and Morgan had broke the bed having sex with someone, I popped wood)
    3) Your place or mine?

    1. PDQ it always tickles me when something I write resonates with a reader. Thanks for taking the time to let me know. Great to hear you married your mate and yes you are a classic Aries! And I remember Morgan and I had to buy metal brackets to fix the bed. I wish that bottom hadn’t heldbon to the footboard so tightly but hey he was the one who assumed that position!

  5. Capricorn10

    Those are ALL very good questions and they seem to prove to be indicators as to what type of dude you are dealing with. I find that your observation and at times introspection is true to what ever subject you are speaking on and as a true Capricorn , you are right about how we can be. I will revisit this post once I start to date again.

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