Why Playing Hard To Get Never Works


Pilot Girl asks:

I met a guy a few months ago through a friend. He's a little younger and works crazy hours in the investment banking industry. I wasn't interested at first because of the age difference. I turned him down a few times before finally agreeing to go out with him and almost cancelled our first date. I'm glad I didn't because it went really well and we had a really good connection.

He was very consistent about seeing me again and again. He didn't let more than a day go by without texting or calling to set up the next date. Twice he called me very last-minute to see if I wanted to grab a bite or coffee after work (when his boss would unexpectedly let him go home early). I agreed to meet him both times on the fly and we had an amazing time talking and getting to know each other. But after the second time I let him know that I would prefer a few days notice for dates. From then on he started to schedule our dates in advance.

Here's my issue. He called last Thursday and asked me out for dinner/movie in the next couple of days (our 6th date). I told him I was free on Friday (next day) and Sunday. He replied that either one of those days worked for him and that I could choose. I chose Friday and we made plans.

A few hours before our date he called to say something came up at work and he had to work late. He immediately suggested we reschedule to Sunday plus gave me Saturday as an option too. He caught me off guard so I initially agreed to Sunday as I was busy on Saturday.

Then I thought about it. Something didn't feel right. That saying by Dr. Phil "you teach people how to treat you" popped into my brain. If I let him cancel on me at the last minute so early on in our courtship then will he think I'm a pushover? Lose respect for me? Do it again next time?

It was a very painful decision (because I really wanted to see him) but I texted him back and said I forgot about plans I had for Sunday (lie) and let's try to connect next week. I wanted to send a message that canceling at the last minute was not OK and the consequence is that he won't get to see me that weekend. He texted back right away with "Why are you bailing on me? But OK, whenever is good for you."

He didn't wait until next week to contact me. He texted on Sunday to say hello and then again on Wed evening to see if I was free for a bite (again last-minute because he finished work early). I was happy to hear from him but I was literally in the middle of having dinner with a friend. I told him I was busy and I'll be happy to do it another time. He texted back "For sure!" but didn't offer up an alternative. It's now Friday and I haven't heard from him since Wed. We don't have any plans for this weekend and I feel like I blew it. 

I feel horrible about telling him I was busy on Sunday when I wasn't. I'm starting to think that this disingenuous move derailed our dating momentum. But as a woman who's dated her share of jerks, players and flaky guys I find it hard to strike a balance between being flexible and being assertive. When do I let it go? And when do I put my foot down?

My dilemma is this: Did I do the right thing by making a stand when he cancelled on me at the last minute? Or did I need to be more flexible knowing that his job is very demanding and unpredictable? Who should make the next move? I feel like he's pulling away (maybe due to my perceived lack of interest) and I'm really unsure about what (if anything) to do next. Age: 42




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