Is My Guy Shit Testing Me?

I am currently seeing a guy, for just over a month now (we just recently slept together), and he’s been very disclosing about what he’s looking for. He’s also very up front with his past relationships, what he won’t tolerate in relationships, and so on and so forth. Charles is a Type A guy, successful businessman who demands a lot of things from the people around him. He does not take any crap from people, and is bluntly truthful. We have been very honest throughout our courtship, any questions he’s got, I’ll answer. I’m not one to pry normally, and perhaps that is to my detriment a little bit. I have been called confusing, and been told by this man that he does not know quite where he stands with me. We know a decent amount about our past relationships, my past engagements (yes, “s”, as in 2), and our recent dating history. He is very affectionate, even in front of his roommates/friends, introduces me to new people if we run into them, takes me on dates, usually calls every night, but is insanely busy overall.

In all of his honesty, Charles seems to be almost testing me, and seeing what my reaction will be to certain things. Here are a few examples: sharing about his exes (I realize there’s a reason they are exes, that’s not my concern), talking about past sexual experiences (again, not a jealousy issue), letting me know that he doesn’t find it “appropriate” to continue speaking with someone you previously dated, when he’s involved with someone, and that he will not tolerate anyone who does that. He also will lets me know if someone from his past pops up, FB messages him, texts him, what they want, etc., makes jokes about our future “60 years down the road” (exact quote), and asks me if anyone from my past has contacted me recently.

I have no issue being honest, but I wonder if I’m getting set up! There are others, and of course more details that I could share, but I’m beginning to think him sharing and letting me know that he is expecting these things is his way of testing me. Is this something that guys do? Is Charles testing me with these things?

Thanks, Donna

This is probably my confirmation bias as a male dating coach who listens to women all day long, or as a man who dated 300+ women, but this sounds a lot like the things that women do to test men. And, like you, I don’t like it one bit.

Ready for Lasting Love?
Ready for Lasting Love?

It’s in the asking of the question that the person issuing these shit tests ultimately fails.

No one wants to get hurt.
No one wants to waste his/her time.
No one wants to invest years of falling in love, only to find out that you’re ultimately incompatible.

So what do people do? Little shit tests like this to try to gather information in advance.

In addition to what you wrote above, I’ve heard all sorts of similar tests:

    • 1. So…where do you see yourself in five years? (To ensure he wants marriage and kids.)


    • 2. So…how many people have you slept with? (To ensure he’s not an immoral slut.)


    • 3. So…what kind of car do you drive? (To ensure he’s successful and stylish.)


    • 4. So…have you ever cheated on anyone before? (To ensure he’s not that kind of guy.)



    5. So…are you in touch with any of your exes? (To ensure he’s emotionally available.)

Understand, the ideas behind these questions are actually quite reasonable. It’s in the asking of the question that the person issuing these shit tests ultimately fails.

His answer will tell you far more than I can.

Because if you’re asking these questions, you’re only indicating that you’re afraid, insecure, and mistrustful that you can’t gather information organically over time. Which is why you resort to “interviewing” your date to find out if he/she gives the “right” answers to your questions.

The problem is that it’s awkward. It makes a partner feel like a piece of meat. He/she knows she’s being tested, and probably doesn’t enjoy it.

So I can’t speak to how other people handle things, but as a direct communicator, I’d come out and say it. “Hey, I’m getting the sense that you’re “testing” me on issues of communication and fidelity. Do you want to tell me about issues you’ve had in the past with women? Because these questions feel a bit uncomfortable and inorganic to me.” And then let him speak.

His answer will tell you far more than I can.