When Dating Goes from Sweet to Scary

There is no fool-proof method to handling these types of situations and I am definitely not one to offer advice, but 9 times out of 10, honesty is always the best answer.
A scary man screaming with a bag of plastic over his head

I can’t help but think of those relationships that seem to be straight out of a bad horror movie. At first, the guy is sweet; cooking you dinner and holding the door for you, but soon enough that typical horror movie music starts to play softly in the background. You brush off uncertainty as pickiness on your end but then that scary behavior of his starts coming out. Soon you find yourself running to your front door, locking it behind you, and grabbing the sharpest knife you can find.

Okay, that was a bit of an exaggeration, but we have all been in a similar situation or have dated a guy that falls into this category. He is kind. He is gentle. He’s just…a little overbearing. Text messages throughout the day, “Thinking of you,” “Can’t wait to see you,” “I miss you already.” all seem innocent in the beginning, but soon enough those sweet little memos become obscure and terrifying. All of a sudden, the guy you are dating has a bit of a dark side. “Why aren’t you texting me back right away?” “Are you out with some other guy?” “Do you not even LOVE me anymore?” Back to back texts filled with desperation and accusatory emoticons flood your phone.

I know this guy because I’ve dated him in the past. He gives me the attention I need – crave – and I look forward to texting him throughout the day and seeing him multiple times during the week. But then, after the honeymoon phase of the relationship has ended, they somehow cannot let it go, and flip a switch from loving to obsessive.

I remember there was this one guy, we’ll call him Brian for legal reasons, and he and I went out on a few dates. He was nice and funny and I liked hanging out with him, but sometimes I just needed some space and time to myself. He lived down the block from me at the time, and he would stand outside my apartment building, staring at my bedroom window, texting me, “Why is the light in your room on and you can’t text me back? What are you doing?” I peeked out my third-floor window and saw him, sitting on the curb, staring directly at me.

I knew I needed to end this “relationship” (and call the police), but I wasn’t sure how to go about it. How would he handle it? Would he be understanding? Civil? Or would he wait until I turned my bedroom light out and killed me in my sleep?

It was a toss-up.

Eventually, by ignoring his text messages and avoiding him at the Dunkin’ Donuts, he got the point and moved on to a new victim. But, why do certain guys act this way? Is it a compulsive need to be wanted? Or is it just plain insecurity? I would put my money on the latter.

Sometimes guys get completely apprehensive about new relationships that they do certain behaviors thinking they are being doting and affectionate, when in reality it is viewed as possessive and unrelenting.

There is no fool-proof method to handling these types of situations and I am definitely not one to offer advice, but 9 times out of 10, honesty is always the best answer. Maybe they do not realize how overbearing their actions are or maybe they thought you liked that sort of behavior because you adapted to it well in the first few weeks of the relationship. Who knows. Try to have a conversation first to see if anything changes before you completely throw in the towel.

But, if you see him lurking outside your bedroom window, run.


Writer: James, a Florida native, has moved up to New York City in pursuit of the perfect slice of pizza...and to pursue a career as a writer. When he is not writing, he is reading the latest Nicholas Sparks novel, attempting a Macaroni and Cheese recipe found on Pinterest, or hanging out with friends at a bar downtown.