How A Dating Expert Dates Online

Here are 3 stories of online dating experiences I've had over the past few years.

The first bachelor was Mr. “K”.  At the end of the first date, he walked me to my door, gave me a hug and said, “Call me”.  Five minutes after we said goodbye, he called to say he wanted to make sure I got in safely. He also said he had wanted to kiss me. Aaah…..

When we went on our second date a week later, I found that I was starting to like him. What’s not to like - he laughed at my jokes and said I was gorgeous. At the end of the evening, he gave me two light kisses on the lips and said, “I know you’re very busy tomorrow, but I’m going to call you anyway.” I never heard from him again, until...I put my profile back up three weeks later and he sent an email.

Here is a part of his email:  How have you been? Haven’t heard from you in a while. Guess you forgot about me.  He also left a phone message 20 minutes after he wrote the email. I ignored both the email and the phone call. I was interested in Mr. “K” but I was not going to put myself in the position of getting close to someone who was able to disappear for no apparent reason. Turns out Mr. “K” was not so “Special”.


1. Saying he would call the next day and not following through: If he had simply said, “I’ll call you” and then not called for 3 weeks, it’s possible I would have called him back. We had only gone on 2 dates and if he didn’t want to call for 3 weeks, that’s fine. However, when he didn’t keep his word, I no longer trusted him.

2. Trying to put the blame on me for being not being in contact with him. Sure, he may have been joking. He knew he messed up and was hoping I wouldn’t say anything. If he had kept it real, and admitted making a mistake, the possibility existed that I would have given him another chance.

3. Contacting me just because I put my profile back up.  I don’t think it’s a coincidence that he decided to get in touch with me within 24 hours of my profile being back up. If he was really interested in reconnecting with me, he had 3 weeks in which to do it in, but he didn’t.


The next bachelor was Mr. A.  We had a great first conversation on the phone – he loves to talk and I love to listen. One yellow flag I noticed was that he bragged about his sexual prowess. We met for coffee and conversation flowed easily.

A few days later, he called on Saturday morning to see if I was available that afternoon to go to a high school basketball game that he was possibly thinking of going to.  I generally don't accept last minute dates, so I said I wasn't available.

About a week later, he called at 4:45pm to invite me to a Lakers game that started at 6pm.  I would have loved to have gone, but I didn't want him to think it was okay to always ask me out at the last minute.  I thanked him for asking but said I wasn't available on such short notice.

A few days after that he sent me a “Kiss” from the dating website we’d met on. I didn’t respond and I never heard from him again.


1. Discussed sex during the first phone call and first date. Am I a prude? Hardly, but women want to be with a gentleman and that’s not how a gentleman behaves.

2. Calling at the last minute for dates. This makes a woman think he already had plans with someone else and they fell through, so she’s the 2nd or 3rd choice. If a man is interested, he will not risk the woman being unavailable when he would like to see her, and therefore plans ahead.

3. Not contacting me when I didn’t respond to his virtual “Kiss”.  At that point, I was still willing to see him again. The fact that he gave up so easily tells me his interest level was not very high, otherwise he would have tried to contact me at least one more time.


Bachelor No. 3 was someone I never actually met. Mr. “S” and I had exchanged a few emails when the caption on his profile changed to, “I’m off the market”. He wrote to me and said he wasn’t really off the market, but he didn’t want certain people (interpretation: women) calling him. 

I left him a voicemail with my phone number on a Friday afternoon. Friday went by. Saturday and Sunday came and went. Monday passed too.  5 days later on Tuesday afternoon he sent an email saying he had been busy with work, but he was going to call soon. Okay, no problem, I thought.

Well, the planets must have changed overnight, because when I woke up Wednesday morning, I said to myself, “Oh hell no!” If Mr. “S” couldn’t find a few minutes to call in 5 days, I was out. No one it that busy. I sent him the following email, “You don’t have to call me. I’ve changed my mind. If you’re that busy, I’m not interested.” Donald Trump once said you can tell a lot about a person by how they behave when they lose. The response I received spoke volumes about who I was dealing with.

Mr. “S” wrote back saying work came first and if I couldn’t understand that, then we didn’t have to meet. He said he wasn’t desperate, didn’t chase females and was going to get around to me last. He also said some other things which I won't mention.


1. Changing the caption on his profile so that certain women wouldn’t call him: This tells me there’s drama in his life.

2. Not calling for five days: I understand that when you meet a guy in the offline world, sometimes they wait a while to call because they want to stand out and don’t want to appear desperate. However, when someone is on a dating site, they are advertising the fact that they are actively seeking someone to date. 5 days is just too much when we’re talking about internet dating, especially when 2 of those days are weekend days. This tells me he is probably already involved with someone else.

3. His response to my email: When I told him he didn’t have to call, he chose to respond from his ego. The ego speaks first and the ego speaks loudest. If he had been a gentleman and said something like, “I’m sorry we’ll never have the chance to meet. Good luck in your search.” there’s a possibility I would have been willing to give him a second chance. Instead, in choosing to send a vitriolic response, he confirmed that I’d made the right decision.