Mr. King Of TMI took the 7:15 p.m. train from Long Island to meet me in the bar/lounge of The Roosevelt Hotel.

From his text earlier in the day, I could tell he was not a city boy.

"Do you have any suggestions as to where to go?" he wrote. (Another clue came afterward when he was nervous about hailing a cab.)

I could also tell he was crazy.

When he kept repeatedly texting comments about me being a matchmaker (i.e., “Is that your professional opinion? You must have seen types like me in your line of work.”), I knew this date was going to be torture.

“Dude. If this is all you are going to talk about, I’ll save you a trip. Don’t bother to meet me.” (I tend to use the word “dude” when men behave poorly.)

Since he apologized for “getting carried away” and I was eager to complete my 50th date, I decided not to cancel.

When he first sat down, I caught a glimpse of his grey sideburns.

Ugh, can I leave now? Why has it been so hard lately to attract a guy my own age?! Maybe I should start bargaining with God?

Mr. King Of TMI, with his cute laugh and thick Long Island accent, was probably quite the looker in his day.

In case I did not realize that he is attractive to women, he decided to share some evidence.

First, he told me about his most recent ex, and then the girl he dated who wore too many clothes, followed by the one who left him for a billionaire and then he got into his family.

He mentioned his brother - who went to jail, and his mother - who went to Heaven.

But, oh no, he did not just tell me that his mom (may her soul rest in peace) passed away, he told me her last words on the hospital bed.

As he spoke, I took a sip of my Bellini to avoid looking at his face, which was growing red, and his eyes, which were getting glassy.

Shit. He’s going to cry. Please don’t cry.

“I’ve got to stop or I’m going to cry.”  

Yup, he is crying.

So Date #50, which took place on a couch, was essentially a therapy session with food and drinks.

And, as I have said before, I don’t work for free.

Have you ever experienced a crier on date #1? 

Is crying a deal breaker or is it wrong to make judgments about someone just because they got too emotional too soon?

What do you think?

3six5date's own, Ms. New York writes about her adventure on a FastLife Speed Dating excursion!

Attention speed daters throughout the world: I’d like to let you in on a little secret...

No, I am not pregnant!

But, guess what? All speed dating events are not created equal!

And trust me, as a professional who has worked in the dating industry for nearly seven years, I am in the know!

Recently, I did some speed dating with a company called FastLife Speed Dating -  and I must say, they know their stuff!

To begin with, FastLife Speed Dating chose an ideal location-the back room at Vig Bar. It was a small, intimate setting - equipped with Mr. Cute British Bartender. The venue was quiet enough for daters to hear each other without shouting, and there were only a few random “others” who were not signed up to participate.

Note: In this context, others are defined as non-speed daters or people who have the ability to turn their speed-dating counterparts into poster children for embarrassment.

Thankfully, the company’s hostess was excellent at preventing embarrassment—not that speed dating is really anything to be embarrassed about in the first place! Anyway, upon my arrival, she immediately gave me a big welcome, and made me feel comfortable by explaining how the event would work.

Then - drum roll, please - she handed me a drink ticket!

When considering which speed dating company to use, never underestimate the power of the drink ticket. Recently, I was at a competitor’s event and was horrified to learn my drink was not comped!

The nerve! We all know a glass or two come in handy at a time like this, and when you only have three to five minutes to make a first impression, the last thing you want to do is worry about breaking a twenty dollar bill!

Needless to say, in this instance, I was relieved to see FastLife Speed Dating had us all taken care of.

More kudos to this company because they were super organized. The hostess made sure things started and ended on time, and when that timer sounded, there was no tolerance for lingering stragglers.

Best of all, there were an equal number of men and women—which, for a speed dating pro like myself, is refreshing. True story: I’ve been to other events where I had to sit out my dates with women because there were not enough men participating!

And, mostly, I liked the women better than the men!

Clearly, when choosing a speed dating event, savvy singles should consider: location, customer service, structure, the male to female ratio, and of course, the likelihood for “free” drinks!

Oh, you were wondering about the quality of the speed daters?

That’s for me to know and you to find out! But, just for the record, I did meet someone. And we shut the place down! Surprised? I never was the girl to waste time….

So this is my first date in 10 years with someone other than my ex. 

I have known Mr. Muscles for about 15 years. He was and still is the local boy that all the girls perved on.

I decided to ask him out on Facebook as I figured we had been chatting on Facebook on a fairly regular basis.

He said yes (thank God) and then I started to panic.

WTF do I wear?

We decided to have drinks at the The Ivy Pool, which for all those outside of Sydney is the super trendy rich kids playground.

I arrived an hour before him to:

1. suss out the venue, and
2. to socially lubricate myself with the free drinks on offer.

Mr. Muscles arrives by catwalking his way over to me.

His swagger is well choreographed and rehearsed. He is Tom Cruise cool before the Oprah (link) couch jumping incident.

And he was very comfortable with me and looked into my eyes when he talked…

Which I love.

The only problem was that he kept talking about himself and told me how a group of young girls had booked personal training sessions with him to ultimately perve on his muscles and get stretched out by him.

I smile and nod in between pauses and can not help but tune out and roll my invisible eyes on the inside of head.

He finally stopped talking to gently lay down on the beach cushions to check out all the bikini clad cocktail waitresses and guests around the pool, only getting up to inform me of what he rates every girl out of ten.

Shit, I wonder what he rates me?

He spotted his friends at the bar and told me he will be right back. After strutting his muscles around the pool for the greatest distance possible, he greets his friends with high-fives and lows, orders drinks and sits down with them.

I take this as my cue to leave.

As I walked to my car, I could not help but wonder why the heck I would meet him at The Ivy Pool - the biggest ‘meat market’ in Sydney.

Was I testing him already? Is that entrapment? 

I then realized I have been out of the game for wayyyyyyyyyyyy too long, but all things considered, Mr. Muscles was a great way to get my feet wet.

How do I get my 'groove' back after so many years in 'retirement' mode?

Do you have any hard and fast tips on what not to do when getting back into the dating game?  

What do you think?

I was really surprised when I got his call.

Almost a year had passed since we first met.

As I remembered, we had a good chat then, and both of us got each other's mobile number in the end. But, I never heard from him after that first encounter so soon forgot about him.

No big deal.

When he called, he asked whether I remembered him.

"Of course." Yes, I remember him quite well.

He was a lovely person; I had just put him in the nothing-will-happen box.

At dinner, after a few rounds of "what's new" small talk, I finally asked, "Why did you call me?"

"Why not?"

A non-answer answer.

"Come on." I was not easy to humor. "It’s been a whole year and we've never talked or met up. You didn't call a year ago. Why now?"

"I was busy."

"For a year?" I replied with a smile.

"The truth is, I was busy at the very beginning. Then when I had time it seemed as if it had been too long since the day we first met. So I hesitated. Then more days passed and the idea of calling you became more and more awkward." 

I nodded. It sounds very reasonable.

“But, why now?"

"I found the piece of paper you wrote your number on inside my wallet last week. So I had a proper answer to give you when you asked me why I called now," he said, laughing.

He was being cute. I laughed, too. But I could not help wondering how many love opportunities I had missed this way.

"You had my number, too. You didn’t contact me." He was giving me a hard time.

I shrugged. "I am a woman."

Should it always be the man who initiates the relationship?

Or is it best for women to sit tight and wait?

Do you think a woman can and should call a man?

What do you think?