Ask A Guy: What Does It Actually Mean If A Guy Says You’re Messing With His Head?

Via iStock

Via iStock

Hi Joel,

I just have a quick question. What does it mean when a guy says I’m messing with his head?

There are a number of phrases that are used far too often between people, and that one is very close to the top of the list. It can be used in almost every era of a relationship, and the meaning behind it is almost 100% based on context.

If this was something said to you by a friend, that is to say anyone you are not in a committed relationship with, he may feel that you’re sending him mixed signals. You may be flirting a bit too much from his perspective or coming off as more than “just a friend,” but at the same time insisting you only want to be friends. The line between friends and more than friends is very very thin, and the more it is blurred, the more confusion can creep in.

When you are in a committed relationship with someone, there are countless other ways that this phrase can be used, and it can lead to big time fights and even breakups. This can often revolve around the way things are phrased, or how seriously he may feel you are committed to the relationship. This is without question the most sensitive scenario in terms of feelings, so tread most gently when trying to resolve things if this is your case.

Finally, you may have broken up or had a short-lived “thing,” and now he feels like he can’t get a clear read from you. If you’re done, but call/text a bit too much, or have long, introspective talks, this absolutely sends mixed messages and can mess with his head. It may be unintentional, but this is very common in amicable breakups.

Regardless of which perspective he is coming from, it is both of your problem to get things worked out. What you really need to do is find some quiet time with him and ask him more specifically how he feels you are messing with his head. Once you have an understanding of what exactly he feels is inconsistent in your message, be very clear about how you feel on that subject, and hopefully you can both move on and get your relationship back to normal.

Best wishes,


Joel Freimark has done a lot in life and seen even more. From last minute international travel to bizarre places to writing award winning books, he’s here to bring his wisdom to all your problems. He hosts a weekly advice series on Youtube and a music series also on YouTube. No question is too outrageous or personal, so go ahead and fire away! Follow him on Twitter.

Are you confused about a guy? Do you find yourself wondering, “What is he thinking?” Tell us everything in the comments! And if you have a question for Joel, email him at!

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