3 Dating Rules I Broke When I Met My Fiancé

Pup waiting patiently for a walk in the background.

Pup waiting patiently for a walk in the background.

If you’ve been with me for any length of time you know that I don’t really like to play by the rules. As Marilyn Monroe said, “If I’d observed all the rules I’d never have got anywhere.” 

Well, If I’d observed society's unspoken rules of dating, then I'd never have met my person. Nor would I be able to help hundreds of people change their dating trajectory after a divorce. 

Here are the modern dating rules I broke:

Rule #1: “Wait for the man to ask you out.”

Society has taught women that men should make the first move and it’s the woman’s place to wait around and be patient for a man’s attention. This mindset puts the burden of taking any action on men, making them feel like they need to do all of the work in order for things to go well in their relationships. It also reinforces patriarchal norms which are not always beneficial for men either. 

Women have been conditioned over time into thinking that if a man does not ask us out, he just isn’t interested. In reality, he could not be asking you out for a number of reasons. Men fear rejection just as much as women do and in some cases even more, as it isn’t considered “masculine” to be upset when you are rejected. 

I broke this rule two years ago when my friend canceled plans at the last minute and I had a Saturday evening free. I didn’t want to stay at home alone, so I asked the handsome bald gentleman who I’d just matched with that day if he wanted to grab dinner. So, we did. 

Ladies - asking a man out first, does not mean you won’t be pursued by the right man. Dating is a dance. #sadiehawkinsofdating 

Rule #2: “Only go out with people who are your “type”.”

We’re all guilty of falling for the same type of person in different forms and then wondering why our love life isn’t going the way we planned.  Which is why one of my top 5 suggestions for things to do after your divorce is to date outside of your previous type. 

I recommend going on a date with someone who is the COMPLETE opposite of your ex. Even if your ex was your exact “type” this is an important exercise. I am not advising that you go out with someone you find unattractive, but he or she needs to be different. 

People evolve. 

What you were looking for when you met your ex has probably changed too. You owe it to yourself to broaden your horizons to see who else is out there and what you may have missed before. This is a first step towards really understanding what your ideal match and future look like.

Back to that handsome bald gentleman — before my divorce, I had never dated a man without hair. 

In previous relationships, I never felt mentally stimulated. I found myself annoyed that my partners did not have the interest in discussing social justice, politics, and other issues that I did. This is one of the reasons that post-divorce, I was determined to date…well every type of man I could. At that point I’d had several failed relationships, so what did I have to lose? 

I know many clients who set limitations (especially on dating apps) and completely disregard a potential date because they don’t tick every box. In reality, these are people, not an order from GrubHub. Order from a different restaurant, and the change might surprise you for the better. 

Rule #3: “No instant connection? No 2nd date.”

As a dating coach and matchmaker, I’ve gotten the statement, “There was just no connection” more times than I can recall. My response is that connection is something you have with someone you have a relationship (or some sort of rapport) with. You have a connection with your friends, family, and that person in the office you like to shoot the shit with when you should be finishing that report.

You will not have a connection right away with an absolute stranger AND THAT’S OKAY!

You don’t want the fireworks.  Fireworks don’t last. What you want is the slow burn. Or what I like to call the sparkler effect*. 

My advice is to give the date a second, maybe even a 3rd shot. If you don’t feel a spark between you after this, then you can send a thank you, but no thank you text. In case you missed it, here’s our guide to not ghosting

When you're deciding whether to give someone your number or go on another date, it might help to ask yourself these questions:

  • Did the conversation flow easily?

  • Did you find him/her interesting?

  • Do they make you smile?

  • Do they seem like they want to spend time with you?

My fiancé and I’s first date was a disaster. To be honest, it was partially my fault. I had not done the work and healing I needed and found myself directing all of my disappointment in previous relationships onto my dates.

Yikes, I know. 

My fiancé and I are both incredibly sarcastic people. In fact, that’s the only thing I really liked about him when we first met. We bantered for 6 hours. He walked me to my Uber at the end of the evening and I went home.

Final thoughts

If you’re waiting to be swept off your feet like a Disney princess, you better go to Disney world and get that shit out of your system. 

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