What It Means When He's Super Possessive, As Told By A Nice Guy And A F*ckboy

by Adam Shadows
Kylah Benes-Trapp

Hi Nice Guy Bobby and Fuckboy Treez,

I'm "Just An Average Janee."

Do you know the saying, "slow and steady wins the race?"

I'm a turtle when it comes to feelings. I don't know how to flirt. I'm an awkward turtle. And I'm pretty slow. It takes me a while to figure out what the hell I want. I don't really know how else to put it.

But when I meet a person of interest, and I find out more about that person, eventually, I fall head over heels for all this person's values and faults.

And boy, I fall hard. I don't show it, though, because of my pride and stubbornness. It's a weakness, but I feel naked when I trust my heart with anyone other than myself.

Well, once upon a time, this guy Aiden* and I met through mutual friends.

He and I had something good. I never pushed him about labels or what we were. I didn't mind not defining whatever we were doing because I was fine with how things were. My friends would ask me if he was my man, and I would just shrug. I didn't care what anyone else thought.

But at the same time, he was possessive and jealous, like a boyfriend would be. He would say that I was his, and I would reply that I just wanted it to be us.

When he asked if I was interested in other guys, I would tell him I didn't give a fuck about any other guy but him. Then, he would laugh and give my neck a few hickeys.

We talked all the time. He was my first text in the morning and my last call at night. I'm a private person, and I despise video calls, but he even convinced me to freaking FaceTime. We ended up going to bed hugging our computers and phones when we FaceTimed each other until we fell asleep.

I fall head over heels for all this person's values and faults. And boy, I fall hard.

I know at this point you might be saying, "OK, Janee, what's the problem?"

Every day, he would ask me how I could like him. He would question how someone like me could even be talking to him and like him. Every time he brought this conversation up, I was taken aback and pulled away a little. I wasn't a fan of him doubting what I felt.

Then, one day, he said he wanted space. My stubborn ass read the message but didn't reply, call, FaceTime or anything. Instead, I dove into my bed and stayed there for the following day.

I know it's not healthy, but I just wasn't the same. I faked smiles and laughs and waited for him to apologize or explain what the hell went wrong. I thought I deserved a phone call at least.

Where did I go wrong, guys?

Kylah Benes-Trapp

Hello "Janee,"

I think I know what's going on here.

The guy is INCREDIBLY insecure. Like, very, very, very much so. You're totally justified in being skeptical of his persistently asking why you like him, especially when he does it so often.

But I don't think he's hiding anything from you. I think he genuinely likes you, and his own insecurities made him question your feelings for him.

This kind of behavior is usually evident in somebody who's been in a few shitty relationships, which is why I believe he wants space.

His own insecurities made him question your feelings for him.

To further defend my point, I want to mention how you said he was possessive “like a boyfriend.” Being possessive is a trait resulting from a man's insecurity. He feels like you can do better than him, so when you talk to another dude, he feels threatened.

Since no man likes to feel threatened (it's a critical hit to his machismo), he seeks possession of you — or asks if you're interested in other guys — to reestablish his masculinity.

But whether he wants to admit it or not, this guy isn't ready for a relationship. He's too insecure in himself. He sees you're treating him well, and it's freaking him out, especially because (as you said) when you do fall for a dude, you fall hard.

He sees you're treating him well, and it's freaking him out.

Things got too real too fast, and he's shaking in his boots. And because I already know this man is immature (I mean, he gives you hickeys, which is kind of childish, high school behavior, and it's something that leaves a visible mark, telling other men to back off) he ended things through text.

Unfortunately, we're the generation where a text message has become a totally acceptable form of communication, no matter how severe the message is. And since you two weren't exactly exclusive, he likely felt a text was adequate.

So for you to ignore the message is both questionable and ultimately ineffective. If you really want the answer: You need to message him yourself, girl.

I can tell you what I think went wrong, which is what I've done (he's too insecure), but as far as giving you real answers to this exact situation, I think you need to confront the man, and get those answers. After all, he did make you FaceTime with him when you didn't want to, so turn the tables on him.

If he can't man up and understand you like him, regardless of how he perceives himself, then it's his loss. He's lost something good and genuine, and it's totally his fault.

He's lost something good and genuine, and it's totally his fault.

Personally, I think you dodged a bullet because dating a man this insecure is usually miserable.

Honestly, there's a very good chance he wouldn't let you go out with your girls in fear of another man approaching you, and you would have to reaffirm your feelings for him whenever he felt threatened.

Basically, he would want to chaperone you everywhere you go, even though you've given him no reason not to trust you.

If that's what you want, then confront him. If not, let him go.

Best of luck!


Kylah Benes-Trapp


He probably left because he felt burnt out, because he missed his old life or because he felt the enormous pressure of spending every day with you starting to weigh on him. You know, the normal shit.

What's more interesting to me is what you did to begin the relationship, not to end it. That's where you went wrong — you picked a jealous dude. You knew you were doing it. You recognized it, and then, you still doubled down.

This relationship was always going to end, solely based on how you started it.

I have sympathy for women who have to tolerate jealous dudes, but not for women who don't realize they DON'T have to tolerate jealous dudes or who convince themselves the possessiveness is some sort of warped token of their SO's love.

I have to echo what Bobby probably already said up top. This guy's behavior is not “like a boyfriend would be.”

Most of us have something wrong with us, sure. But not all of us believe we own the women we date or that we can control them and dictate their actions.

In fact, a lot of us want independent women who live full lives of their own desire. A lot of us want to be passengers along on their ride, not asshole kidnappers driving a white van, dragging you along a life you don't want to live.

Jealous, possessive men are small men. They stroke their fragile egos, bathe in self-hate and lack the ability to project that hate anywhere but outward.

Jealous, possessive men are small men.

They think it sucks for them, when really, it sucks for the rest of us. Their insecurities seep through relationships like acid until the relationship is ultimately ripped apart.

From an evolutionary standpoint, there are always going to be jealous dudes claiming particular women, no matter how far we evolve, just as there will always be male baboons flinging their shit at other baboons grooming their females. So from that perspective, I kind of understand it.

But then, I see a dude — like my best friends and family members — acting jealous, and I can't help but think it's the most repulsive display of penile-possessing bullshit this side of a Trump rally.

Sometimes, women do push men to the edge, but some men have unacceptably short edges, and we run to them at the slightest bit of trouble.

Sometimes, women do push men to the edge, but some men have unacceptably short edges.

It's gross that one of the reasons I avoid commitment of any kind is because I don't want to wake up one day and find myself acting like that. I know I'm not nearly the best thing for them, but I'm also afraid to see anything worse than me befall them. And there is worse out there.

I know you came to me for answers, Janee, but all I really have are questions for you. I don't understand women who stay with dudes like this, so please explain it to me.

Did you like being controlled? Or did you just think that was how things were supposed to be?

Did you just like the feeling of being with someone — anyone? You said you usually try to avoid that, but then, you were devastated when you gave in and it ended.

So what did you like about it? What were the positives, and how did they outweigh the negatives? What does that say about you? And what can you take from it moving forward?

In the meantime, my advice is to say fuck that dude. Fuck him for being that way with you. Fuck him for tricking you into thinking you're not better off without him. Fuck him for perpetuating one of the ugliest male behavioral traditions.

Fuck him for making the rest of us look bad.

Unfaithfully yours,


*Name has been changed.