He's having a lot of trouble getting her out on date 1 - does he need patience or does he need to give up?

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Hey Doc,

I need some confirmation that I’m thinking about this situation in a “System” manner.

I am a Salsa dancer in Ohio. I go out to a lot of dance events each month, so I have a chance to meet lots of women. One woman in particular, Leila, has been giving me subtle buying signals for a year. I was involved with someone else up until a couple of months ago, so I couldn’t ask for Leila’s phone number until we broke up. I went to a dance event last weekend, saw Leila, and asked her for her phone number. She gave it to me without hesitation and said that she was glad that I asked.

I waited five days and called to ask her out for this coming Tuesday. The phone rang twice and went to voicemail. I left a voice message in which I said I’d like to take you out, so please give me a call. My number is…. Then I repeated the number slowly and hung up. While I was leaving the message I received a text back that read “Sorry, I can’t talk now.” I’m guessing this was an automatic text response Leila set up for any incoming phone calls. A few hours later she sent me a text message that said that she had been involved in a local city meeting when I called, then she went to dance practice, and due to the time of night she was sending a text instead of calling. I figured it was no big deal.

Leila called back the next day. She asked if I had received the text she sent, and I thanked her for letting me know what was going on. I then asked her out to dinner for five days later. She checked her schedule, said that she had a scheduling conflict, but immediately counteroffered with two other days but she said one of the days was contingent on whether her stepdaughter would visit, and that on the other day she could only be up until 9 PM. I said “Just let me know when your stepdaughter lets you know if she’s coming and get back to me when you know.” She said she would. End of conversation.

Leila texted this morning that she still wasn’t sure if her stepdaughter was coming, but that she would be amenable to getting together around 6 PM. The condition attached was that she wanted to stay close to her home in case her stepdaughter showed up. She then added that we could take a walk or go to another restaurant, because she didn’t like the eatery I picked for dinner.

I haven’t responded yet. I know you’re big on getting in front of the girl for the first date to try and sell her, but it seems to me that Leila is probably either (1) structured and/or (2) she has low Interest Level.

So Doc, how do I respond? It seems like it might be a major waste of time if I go along with her.

Oren - who doesn’t want to waste his time

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Hi Oren,

When Leila said she could meet you until 9 PM, that was the definite date and the one you should have grabbed. What you did instead was take the “definite maybe” date involving whether or not Leila’s stepdaughter was going to be in the picture. Why would you do that? It was a huge blunder, pal. You had a sure thing and you had a definite maybe. You jumped on the wrong one.

Oren, there’s an entire chapter in the Dating Dictionary that says YOU DON’T MAKE CALL-BACKS TO VERIFY DATES. And you did that, which means you are not operating by the rules of “The System” at all!

Then Leila had all kinds of conditions attached to getting together with you. All this woman is giving you...

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