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The Dilemmas of Date 1

On Friday, I was in the midst of an "emergency call" at 7pm with a Sydney client of mine as she was grappling with a number of dating dilemmas and in need of urgent help.

Cynthia is in her 30's and only very new to Rules dating. This was her very first Date 1 with a guy she'd met just over a week ago at speed dating. She had already been struggling all week with allowing him to take the lead with setting up the date because it was taking so long for him to just get all those details out there to her. "Why did it have to be so hard with all of this back-and-forth tennis match just to get to the time and place?" she said.

The Date 1 was a Friday night because another guy she'd met at the same speed dating event had already pinned her down for Saturday night. Cynthia had also agreed to meet him in the city, as she was working in the city that day and she thought it would be convenient for her. I explain to my clients that the location of a date is about your convenience. You don't want to find yourself in a situation where you're running around like crazy, rushing to get ready for a date and then travelling long distances to get to him. Remember, men take about five minutes to get ready. Women take one hour MINIMUM, some much longer. And also a good guy appreciates the journey, the effort, of coming to where you are.

Cynthia began emailing me around 6:45 pm. She'd only just received a text from him:

I told her to reply with "I don't have WhatsApp. Soon would be great for me." He had previously planned to meet her at Town Hall Friday night after work and I figured that he'd been trying to plan the time with her on the day, sent her a message on WhatsApp and it took far too long to dawn on him that she didn't have WhatsApp. Sometimes guys can be a bit slow in that respect. They're so used to everyone being far too accessible.

He replied:

By this stage, Cynthia was ready to cancel the date.

I called her as soon as I could, to hear what she had to say. This was her first Date 1 so I wanted to talk her through everything.

Cynthia was angry with this guy that he'd left it so late to get in touch with her. She was also very stressed, as she left work at 4:30pm and caught the train home to shower and dress up more comfortably. She was now on the train back to Town Hall and ready to tell him to forget it.

I explained to Cynthia that this was inconveniencing her terribly and tried to get to the bottom of why she'd agreed to meeting in the city for dinner if she was finishing work at 4:30pm. She replied that due to the heat and humidity here in Sydney, she didn't want to turn up to the date feeling unclean and wanted to get dressed at home. She left work early to do that. Together, we came to the conclusion that, as she doesn't have anywhere to shower and dress comfortably in the city, all future dinner dates should be near where she lives rather than close to work. Again, it's all about her convenience and all this travelling back and forth was too overwhelming and far too much trouble to go to. It would have been better to go home and get ready at her leisure so she was not feeling rushed and off-balance when she arrived at the date close to where she lives.

My clients who have been dating a while have this mastered. Experience shows them what works for them in getting ready for a date. For some girls, it works to meet close to work for dates. They have a gym nearby or facilities at work where they can get ready comfortably. Cynthia has discovered that going home works best for her. I mentioned to her that any future dates with this guy will be Saturday night so she wouldn't be meeting him in the city anyway.

The next dilemma was that she was angry with him for telling her the time too late. I asked her to go easy on him for this. Clearly he'd been trying to get in touch earlier to set up the time and he was trying. Cynthia also knew that most guys can't set up a date at all and the fact he got this far puts him above 99% of guys out there! I told her that this date was a bit "all-over-the-place" tonight but she's learnt a lot of lessons and next time, it will be much more streamlined and she won't find herself in such a predicament. No more dates in the city and no more WhatsApp issues.

Cynthia relaxed then and agreed to text him back, "I'll be there at 7:30."

He replied with a specific place for them to meet.

I told her to relax now, breathe and to email me later with the wrap up of the date.

This was what she wrote to me later that night,

Hi Lynda, Thank you so much for hand-holding me this way tonight, I am very very grateful. This whole experience has opened up my eyes. In the past, I would have felt angry, walked away and left the poor guy stood up for the date.

Thank you for reminding me to stay light and breezy. Sorry for this slightly long email tonight. I thought I wanted to share what I'd learnt.

After our phone call, I turned up and Rob was waiting right outside Haighs. He suggested an Indo-Chinese restaurant or that rooftop bar for dinner but somehow he decided we should go with the restaurant. The restaurant is not a fancy one but I really appreciated his planning. He may have thought the rooftop bar was too noisy for us.

I did not mention a single word about him not giving me the exact time of the date. I stayed light and happy.

The whole time I thought about how you'd been telling me when we don't ask men anything, they disclose things themselves willingly. This is so true.

He said he went home after work and waited for my WhatsApp reply for a long time but heard nothing. He said he then realised we did not set a time and I probably don't use WhatsApp, hence he SMSed me instead.

I met him at 7.30pm and we finished our food by 8.40pm. He asked if I would be keen for dessert but I politely said I am full and I have to get going. He paid for dinner and I thanked him.

He walked me back to Town Hall station. When I said bye to him, he said, "I look forward to catching up again." They all say that but many never follow up so I just said, "Sure, sounds great."

After I got home, he texted me. I've attached the screenshots. I am not sure if he is going to ask for future dates but I will keep you posted ok?

I am glad I went with the dress you chose for me this morning and listened to your advice to go ahead with the date tonight.

It may be too early to tell.... but Rob turned out to be really nice so far. Thank you for handholding me so patiently each and every step Lynda!


It takes a while to get into the flow of dating. It's so radically different from what's usually going on out there, like cosy Netflix dates at home instead of dinner dates. Just stay with the program and you will eventually see results.

As they say, all good things take time! (And patience - and healthy boundaries.)


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