My Sex in the City Dating Life

True stories of what NOT to do on a date.

Date #1

Mr. Return-Of-The-Mack

He told me to stick with him and he would bring me from down there to up here as he motioned with his right hand the distinct difference between the two levels.

This was before we even entered the restaurant. In fact… this was in the parking lot and within the first few minutes of our date.

It was our first date, and it was off to a great start. Maybe he thought he was being funny?

I gave it a chance but made a mental note to have separate bills. I like to pay my own way, especially if I don’t think it’s going to work out.

I was right, the conversation had an ‘I’m so lucky to be there with him’ vibe.

There wasn’t a second date, nor a third. He seemed genuinely surprised.

Dating Tip

Be humble, it’s not necessary to show off or try to force the other person to see your best traits right from the start. Treating your date with disrespect will ensure you miss out on the second date. The other person would like to get to know you organically. Arrogance is one of the biggest turn-offs, and FYI, please… don’t insult them.

Date #2

Mr. Al Quit-Smoking Pacino

I once met a fellow at a nightclub where I worked. It was a busy night and people were socializing, dancing and drinking. This one particular guy seemed pretty chill and was sitting off to the side on his own. He looked like a young version of Al Pacino.

I found out he was just waiting for his brother. I wouldn’t normally go out with a customer but I made an exception as he seemed so normal… compared to the drunkards at the bar.

We went on a few dates, drinks with a friend of his, a walk around the sea wall, and then a bus ride.

I’ve never been overly materialistic, and the simple dates were nice. Things seemed to be going well. On our 2nd date, I noticed he snuck on the bus without paying. I called him out on it and he said he never pays for the bus. I was embarrassed but laughed it off and silently reconsidered my dating choices.

On our third date, he asked if I would buy him cigarettes. I surprised myself by saying no. Then made an excuse shortly after to go home early.

There wasn’t a fourth date.

Dating Tip

Before we go out with someone else it’s important to make sure we are in a good place ourselves. Depending on the other person, you don’t need money to have a great date. A blanket, a beach or a park with candles, coffee and conversation can be lovely. But if you’re in a place where you need to borrow money, then be sure to borrow it from someone else before you go on your date.

Date #3

Mr. George Nar-Co

I was pretty young at the time, and I had a date to meet a fellow at the mall. He was a little older, but not by much. He seemed quiet but also had an interesting look about him. I gave him my friend's phone number because I knew my mother would never approve of him. I had never gone out with someone like him before. He seemed different, but I couldn’t quite put my finger on it.

So we just walked around the mall which is what we did in those days in the town we lived in. He took my hand to hold… so cute… he seemed pretty nice and kind. That is until we met up with someone to who he sold illegal narcotics… right there in the mall alongside me.

I don’t remember much else after that, except making an excuse and leaving pretty quickly. My friend told me he called after that first evening looking for me a lot. I never saw him again. My mother would have been right.

Dating Tip

Don’t sell drugs. Don’t sell drugs when you’re on a date, don’t sell drugs at a mall when you’re with a 16-year-old girl. Just don’t do it! He was so darned cute otherwise… Sorry…not sorry George Nar-Co for ghosting you.

Date #4

Mr. No-Thanks Buttery Fingers

I was on a date with another potential love interest. I was in my mid-20s and he was quite a bit older. He was interesting, he seemed confident without being arrogant. Our date seemed to be going well. He was charming enough with a fun personality. We were having a nice time. You could sense his experience with dating, and he was much more worldly than I.

It felt like such a normal date. Dinner and a movie. He insisted on paying and I accepted because he was quite charming.

Unfortunately, at the movie theatre, he ordered coffee with his popcorn.

Coffee??

Okay so this is a Seinfeld moment in which I’m somewhat mortified by that, but hey… maybe that’s what 40-year-olds do at a movie theatre!

I wasn’t expecting what came next part-way into the movie… he tried to feed me popcorn and lecherously ran his fingers inside my mouth.

No!!!

This was obviously a sexual gesture and one which he no doubt wanted me to reciprocate. Well reciprocate I did by turning my head, pushing his hand away and making an ick gesture of my own.

Maybe he felt entitled?

Sorry… not sorry Mr. Buttery Fingers.

He also seemed genuinely surprised by my turning down a second date.

Dating Tip

Don’t try so hard to show your interest. It can come across as cringe-worthy. Not to mention that a stranger isn’t going to want your fingers in their mouth within the first 3 hours of the date.

Also, coffee and popcorn do not go together, not then, not now, not ever.

To keep a date going well, maintain a certain level of respectable distance. Any kind of overt sexual gesture could be a huge turn-off for the other person. If things are going well, then hold onto that particular energy.

If you’re second-guessing something, such as sticking your fingers in someone’s mouth, best not to do it at all.

Date #5

Mr. Beverly Head-For-The-Hills Cop

So we were set up by a coworker where I worked. He wanted to take me out and asked her if she thought I would be interested. He was a police officer. He didn’t seem like a very happy person but I figured why not?

I was in my mid 20's.

We made a coffee date at Starbucks. He was already there and sitting at a table. I went to the counter to order and noticed he didn’t have a drink. When I asked him if I could get him a coffee he said no. I figured at some point he would have gone up to get something to drink, or eat…

After some time passed I asked him again if he was going to have anything, he told me he didn’t drink coffee, tea, juice, alcohol or pop. He only drank water, but he chose not to drink water that day either.

Well, that’s odd I thought, but not the end of the world.

So I drank my coffee at our Starbucks table while he had nothing.

Awkward…

Trying to be polite and pretending not to notice how bizarre this was, I asked him what he did for fun, or if he had any hobbies. He said no. Not really. This date was going from bad to worse.

I asked him about his job and his answers were pretty short and generic.

We sat at Starbucks together, with one drink on the table. He spoke about nothing and watched me drink my tea.

I left once I couldn’t bear it anymore wondering why he wanted to go out with me in the first place!

My appearance was the same, my personality was polite and charming, and I wasn’t loud or obnoxious. I was the same at the coffee shop as I was at work. I was so confused.

Dating Tip

You cannot, I repeat, cannot go on a date without ordering anything. It’s weird and anti-social. If by chance you’re feeling off, or if you had a bad day then it’s okay to call and ask for a rain-check. It’s always best to go out with someone you’re interested in when you’re at your best. And always, always at the very least order a tea.

Date #6

Mr. Humphrey Braggart

So I was at a restaurant with someone I had met. He seemed quite nice, and he was, for one small exception. He bragged all the time. He had this, and he had that… he was this, and he was that. He was another one who gave off ‘you’re so lucky to be with me vibes’.

I can still to this day mimic how he would give a deep, low, grunt-like exhale when he told me how great he was, and how rich he was.

To make things worse, he put down other people, a lot. He laughed at people less fortunate than himself while ensuring everyone around him knew how wealthy and amazing he himself was.

Ick.

“Pride makes us artificial and humility makes us real” Thomas Merton

Dating Tip

Refer to the first tip. Be humble. Your potential love interest will be far more interested in you if they have to search a little to see how great you really are.

Date #7

I met a man and went on a date. He had a perfect combination of charming conversation, wit and fun. He was humble, not arrogant, he asked me a lot of questions, and was genuinely interested in me and what I had to say.

We went on a second date and a third…

Eventually, he gave me two beautiful children, and it was the last date I went on.

Although life happens and we’re no longer married we are still a strong family of four. I will never regret going on that date.

Sometimes it takes many, many ‘bang your head against the wall’ popcorn and coffee drinking narcotic dealer dates to find that perfect fit.

Never give up.