I had a boyfriend for 2 years but I hadn’t been on a real date since the last guy I dated a few years before that.

How does that work?

I was dating an executive.

“What’s a REAL date?”, he asked defensively when I proclaimed that he’d never taken me on a real date. It was as if I had just accused him of having a small penis.

He said he always pays when we go out to eat. Wasn’t that enough? No, Ben. Its really not. Especially since we only go out to eat at fast food restaurants and I always drive. He was always planning things at work and he didn’t want to plan dates too. I wasn’t having it. Planning a date once every few months is not going to kill a man.

So what are the ingredients for a REAL date then? Here are the rules…

1) He picks the location. All by his big boy self. He picks it and tells you where so you know if you should be wearing your Christian Louboutin pumps or your Michael Kors sandals.

2) He picks the time. You don’t look up hours of operation. You don’t help him make reservations. He tells you what time you need to have your eyelashes glued on and your contouring done.

3) He picks you up on time. ON TIME. I don’t care if he’s from out of town and doesn’t have a car in your city. We do not live in the stone age. There is Uber, car rental companies, and primitive yellow cabs. Expect him to figure it out. You’re not being high maintenance, sweetie. I promise.

4) He pays the bill. There really shouldn’t be any question about this. If he is taking you out on a date and you pay the bill then is he really taking you out on a date? It’s not a philosophical question. You can and should pay for dates too, but not the ones he plans.

Now, I know what some of you are thinking. “What if he takes me to a restaurant with horrible food?” or “What if he just takes me out once and expects a gold star?”

My response to both of those questions is going to be the same. Give him that gold star IF he shows up on time and doesn’t complain about organizing the logistics of the date. If the restaurant was a bad choice, tell the server why and make sure that your executive hears the feedback the server is getting. Of course, it goes without saying, be polite and provide the feedback AFTER you’ve received your meal. Don’t want anyone spitting in your food. On your way home, ask him what made him pick that restaurant and tell him you don’t think you’d want to go back there again. Then thank him (in your own special way) for a wonderful evening.

See, you’ve got to give him that pat on the back and make him feel appreciated for the gesture of taking you out, even if it wasn’t the perfect date. It’ll make him want to do it more often. And we all know that practice makes perfect.

My problem was getting my executive man to do it the very first time. Here’s how I popped his date planning cherry.

It was simple. I jumped all over an opportunity to call him out in front of his friends. A bunch of us were out one night celebrating his sisters birthday. One of his friends asked where our favourite date night spot is. He looked over at me and I knew he wasn’t going to answer that question.

“McDonalds. We order 2 large fries and an apple pie and we sit in the car and eat our sorrows.” That was my answer. I wasn’t lying…except for maybe the “favourite” part. That was definitely a lie, but that was our go-to date night.

His friend looked at him in utter WTF amazement. I couldn’t tell if he wanted to know my man’s secret for keeping me around for so long or ask me why I was dating this guy. He managed to get out one word, “Seriously?”. Then he said his wife would leave him if he didn’t take her somewhere nice at least once a week. I gave my man a look that read, “Yeah, you got it real good buddy, but that’s all about to change.”.

Bae got the hint.

It still took a little bit more nudging over our next few phone conversations about what we were doing over the weekend before he finally planned a date. It didn’t go very well. I broke rules #2 and #3, and I sorta broke rule #1 as well by giving him two options to choose from. He picked the hole in the wall option with good food because we were supposed to go mini golfing, but he couldn’t figure it out….so we just ate. At this casual hole in the wall spot. And then he never tried to plan a date again…probably because I gave him zero gold stars.

That’s not the reason why I’m not dating him anymore though. Okay, fine it’s not the ONLY reason why I’m not dating him anymore.

Moral of the story? Its more than okay to have expectations and standards. If he can’t live up to them, well, there are executive men out there who can and will.

You’re probably wondering how you can get your perfect opportunity to call him out. Well, its the holiday season. Nothing wrong with planting a question of a similar nature at a festive gathering. 😉

If you’ve got any other tips or tricks up your sleeve to get him to take the initiative to take you out somewhere nice once in a while, I’d love to hear them! Get in touch with me and I’ll feature the best tips on my Instagram page. Don’t forget to include your IG handle for a shout out.

Click here for challenge number 7!



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