This is Rachel’s date 4 with Mr. Kind Of A Big Deal. Read their date 1,date 2,date 3. It has been nearly four months since I last saw Mr. Kind Of A Big Deal, despite his

This is Rachel’s date 2 with Mr. Seems Great To Me. Read their date 1. Mr. Seems Great To Me is truly a catch – he is smart, fun, and adorable – complete with dimples and

This is Rachel’s date 3 with Mr. Potential Dream Partner. Read their date 1,date 2. Mr. Potential Dream Partner emailed me to ask what I was in the mood to do for our date. I wrote back:

This is Rachel’s date 2 with Mr. Potential Dream Partner. Read their date 1. A bit before the end of our date, Mr. Potential Dream Partner (Date 75) told me he had an amazing time, better

Just a couple of days before we met, Mr. Potential Dream Partner randomly emailed me stating that he found my website and wanted to “meet for a drink to discuss synergies between our practices.” Yeah,

Tonight’s date was far from typical. By the time I arrived at Accademia di Vino, I already had a buzz. While I have been known to schedule a few nights of back-to-back-meetings with clients,

As I sat in the parking lot of Positano Restaurant waiting for Mr. Worth A Second Glance, I reflected on how much dating has changed over the past few decades. The night before, at my

This is Rachel’s date 2 with Mr. Surprise Surprise. Read their date 1. Okay, so I kind of like Mr. Surprise Surprise. I like his authenticity, his Long Island accent, the way he put his hand in

At dinner, my girls wanted to hear how date 71 went. “It went well. I liked him – I mean as much as normal for just having a brief meet and greet.” Okay, maybe I liked him

According to Forrest Gump: “Life is like a box of chocolates. You never know what you’re going to get.” This seems like the same case when it comes to online dating. It is not that

From the very first night we met, Mr. Not Just Another Guy was special to me. Somehow, two nights ago, he got through my I-don’t-hook-up-with-guys-so-soon wall. I felt comfortable with him from the start –

This is Rachel’s date 5 with Mr. Made Me Comfortable. Read their date 1, date 2, date 3 and date 4. A few months ago, after our fourth date (date 45), I told Mr. Made Me Comfortable I could not

In the past I had a tendency to be attracted to men who were somewhat “broken”—not complete disasters—but diamonds in the rough. The rescuer in me used to think it would be very rewarding to

Mr. My Last JDate wanted to meet at 10:30 p.m. I told him I needed to push the date back a half-hour so I could finish up some work. Translation: I want to watch Jersey

Have you ever been on a date with someone and wondered if he was really ready for the serious relationship he claimed he wanted? With Mr. Got Me Wondering (Date 63), one of the few