Why I Won’t Date You Again


One of my best friends has been busy in New Jersey for the past month so our usual (re: obsessively daily) FaceTime sessions have been cut short recently and when we do talk, we have to talk about everything that has been building up. A few weeks ago, we were discussing relationships: best dates, worst dates, what makes a good relationship, what breaks a relationship, what annoys us about significant others…everything. It got me thinking about how one person can go from Mr. I-See-Potential to Mr. I-Just-Missed-A-Big-Ass-Bullet and I realized that there are usually critical turning points that cause the interest level to go from “Hi” to “Bye.” While I’m certainly not categorizing all men, these were a few turning points that I experienced.

The Husband: This man’s got the ring picked out before you’ve even had the chance to order appetizers. Labor Day too soon to meet his parents? Not for him. You better go scoot over to Lilly Pulitzer real fast, honey. Every plan involves the two of you, kid talk is on the horizon, and moving in after a year of dating is expected. Not feeling it yet? You run like hell, girlfriend.

The Incident: This man just hits you like a wall and it takes you months to extract yourself from the relationship, look back it, and wonder, “was I drunk the entire time?” or say “I don’t even know what that was.” While it starts off fun, light and casual, soon you find yourself feeling anxious when he no longer responds to your calls right away. It becomes like an up and down drug addiction. You hear from him and it’s like a high and then after days of silence, you’re drowning in depression, waiting for another text. Essentially this is the hit and run of relationships.

The Alpha Male: I get it, bro. You’re dominant and you like your Progenex More Muscle. Every conversation feels like a power play to reinforce that he’s in charge. It’s overbearing, he’s pawing at you and making your decisions for you. What’s even more annoying is his urge to pick a fight with the man who accidentally nudged your chair in the restaurant…like I am really going to go home with you based on your ability to snarl at the hipster in the Pug bar. “Olivia will have an Angry Orchard.” No, dude, what I’ll have is the check.

The Houdini: This guy comes and goes as he pleases. One date, it feels like you have a connection and then you hear nothing from him. Or, you talk for a few months and it trails off, only for him to reappear after a few months with a “hey, you around?” You can’t help but text your best friends with a picture of his message or missed phone call because you know the reply from them is going to be “what the actual #$%^?” Either you’re here or you’re gone, dude. Just because something didn’t work out with another woman, does not mean you can casually crawl your way back into our lives, only to leave when something better (in your mind) comes around.

The Hide Yo’ Kidz, Hide Yo’Wife: This man is married, will most likely have a baby on the way, and is under the impression that a little wild side action is just what he needs before parenthood sets in for real. He’s lied about his marital status, and then there’s that inevitable moment when you find the What to Expect When You’re Expecting book in the trunk of his car just before you two head off for your romantic weekend trip to the mountains. This is the Jeffrey Dahmer of relationships.

The Baby: No matter how old this man gets, at least biologically, he will forever behave like a juvenile and you Mom him like no other. This is the man who requires constant attention and reassurance that he’s the center of your life.  When that doesn’t come, get ready for the pouting. This is also the man who enjoys his video games a little too much, who hasn’t really determined a strong career path, and whines when things or plans don’t go exactly as expected.

I’ve written before that dating is such a delicate dance, and the actual date is only half the battle. Becoming comfortable with opening up to someone is perhaps the hardest part, at least for me. It’s also a struggle to wonder whether to stick it out with someone in the hopes that he or she will change their behavior eventually, or whether to call it quits early on. Listen to your gut instinct because if something isn’t settling with you, then chances are there’s a larger problem going on. Recently I tried to voice my concerns about communication to someone I cared about and I ended up feeling pretty shut down when the conversation didn’t go anywhere. And maybe that’s another turning point for me. 

Watch your six & stay purring,



Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s