Tag Archives: dater x

Dater X: A Great Date & An Epic Fall

Dater X: A Great Date & An Epic Fall

It was only a day or so after things crashed and burned on my date with Jack when OKCupid emailed me a “match,” alerting me that someone was interested. After checking out my match’s lengthy profile, which was refreshing to see since lots of guys write the bare minimum, he seemed to have a lot of potential. He loves dogs, has a great job, appears to share my values, plays baseball, enjoys being outdoors and was pretty damn cute, to boot. I figured it couldn’t hurt to shoot him a message. Just over a week later and after many exchanges back and forth, he asked me out for drinks. Obviously, I said yes. Keep reading »

Dater X: Three Strikes, You’re Out

Dater X: Three Strikes, You're Out

Last week, I went on my first date with Jack, the young publicist I met through work. And after I tell you all what occurred on that date, I’m confident you will understand why my first date with Jack was also our last.

After taking the initiative to ask Jack out, I figured I’d let him take the reins and plan our first date. We agreed to get together after work and didn’t have a game plan, so we decided to just play it by ear. He met me by the steps of the New York City Public Library and was as cute as I remembered, but slightly younger looking (which was probably just my subconscious reminding me that I was a cradle robber). He suggested we go grab some coffee and then maybe a bite to eat afterwards, depending on how we felt. On our walk to get caffeinated, he said, “I’m glad you asked me out. I like seeing a proactive woman who isn’t afraid to make the first move.”  We were off to a great start. Keep reading »

Dater X: My First Younger Man?

Dater X: My First Younger Man?
Dating Don'ts: Younger Guys
Dating Don’ts: Why Dating Younger Is Not For Me
The case against dating younger. Read More »

To give you all an update, my Stage Five Clinger is still clinging. After several days without hearing from him, which was of course the desired result from our very matter-of-fact chat, he sent me a message over the weekend that said “Hey, thinking of you and thought I’d say hi.” I obviously completely ignored his text and and am crossing my fingers that he gets the hint. Besides, I have another prospect in my sights who happens to be far less creepy. Oh, and did I mention he’s also quite a bit younger? Keep reading »

Dater X: We’ve Got A Stage-Five Clinger, Folks

Dater X: We've Got A Stage-Five Clinger, Folks

Like everybody else in America, I decided to jump on the World Cup bandwagon last week and headed to a bar after work to catch a game with friends. When one of my girlfriends showed up with a few of her co-workers, I noticed  that I’d caught the eye of one of her colleagues. Well over six feet tall, he was muscular, well-dressed and had a nice smile, but I wouldn’t say I was necessarily attracted to him. After very obviously staring at me and not at the TV for the next 30 minutes, Ken headed my way and started making small talk. He seemed funny, nice and attentive, so when he gave me his number at the end of the game, I intended on shooting him a text the next day, and maybe even going out on a date with him if things continued to go well. Spoiler: they did not. Keep reading »

Dater X: Getting Back On The Horse

Dater X: Getting Back On The Horse

The first week after a breakup is always the most difficult. The rejection is fresh and the sting still burns, which makes it that much harder to remind yourself that the relationship is over, and that, despite how it feels at the time, things will get better. Those first few days are also crucial in determining how you’ll handle the rest of the breakup. The decision to end things takes only a moment, but coping with that loss can take days, months, or even years. And in my opinion, the tone of that “healing period” is set early on. Will you continue to communicate, cut each other off cold turkey, or decide to have casual sex until he realizes he wants you and only you? After my breakup with Andrew, I chose my path, and thankfully, it resulted in clarity.

When Andrew blindsided me with the truth bomb that he wasn’t ready for a girlfriend, I knew I’d be incapable of carrying on any kind of communication or relationship with him without developing muddled feelings. We both agreed it was best to sever ties. About a week later, I went out with friends for drinks, headed back home alone and found myself aching to text him. Keep reading »

Dater X: A Breakup I’ll Never Forget

Dater X: A Breakup I'll Never Forget
Dating Don'ts: Breakups
These kinds of breakups suck the very most. Read More »

It went as perfectly perfect as a breakup could go, I suppose.

Only a few days after my last Dater X post, when I told you all about my hopes of moving things forward with Andrew, he came over to my place to hang out and, without warning, dropped a bomb on me. As usual, we made small talk for a while, chatting about our weekend plans and jobs, and worked our way into my bedroom. Mid-makeout session, I reached down to unzip his jeans, when his hand grabbed mine and pushed it to the side— a suspicious move for not having seen each other in a week. He sat upright, looked me in the eye and said, “Before we do this, there are some things on my mind that I think we should talk about.”

In that moment, I was sure he was going to tell me he wanted us to be exclusive, and ask me if I felt the same way. Keep reading »

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