Does He Need Patience? | Doc Love - Dating Advice For Men

First Date Issues – Why Won’t She Go Out?



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 is possibilities for definite maybe dates. Like my cousin Fast Eddie Love from East L.A. says, “You can’t pin her down at all.” And it’s impossible to pin her down, with all of the conditions that she’s attached to seeing her.

Of course you have to get in front of the woman in order to sell her. But that’s exactly where you blew it. You had a definite short date versus a definite maybe date in which Leila was more concerned about her stepdaughter than she was with you. Like I said, you took the wrong one.

Leila is both structured AND she has low Interest Level. You’ve gone every which way with her as far as trying to get a date goes, but she always comes up with another reason why you have to call back later, or that she has to wait around for her stepdaughter, or that she doesn’t like the restaurant, etc. 

The point is that Leila is NOT HELPING YOU at all. 

Look at all the time and effort you’ve invested in just getting a first date out of this babe! So if you have to get her out on eight to 10 dates and make her your girlfriend, you are facing a brutal uphill battle, my friend. Leila is structured, she has low Interest Level, and she practically does everything but come right out and scream, “Don’t call me!” Like my cousin General Love says, “It sounds like you’re going to war instead of trying to date this girl.”

How do you respond now? Tell Leila that something came up in your schedule and that you’ll make it some other time. If I were you, I wouldn’t even try to go out with Leila anymore. You can’t get a definite date out of her. It’s too much trouble and work. To you Psych majors, if it takes all this effort to get the first date, can you imagine how difficult the other nine are going to be?

You’re worried that trying to date Leila seems like it’s going to be a major waste of time? Guy, it’s been a major waste of time already!

Remember, guys: when you have to fight to get the first date, you’ll never get to the tenth to make her your girlfriend.


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  • Tony says:

    Doc, maybe I misread this, but it seems that Leila is a poor time manager and is eagerly trying to go out with Oren at the earliest date possible for Oren, and in doing so is trying to deconflict with a visiting stepdaughter. In short, I feel like this is Oren’s fault for not countering with a later date in which the step daughter would not be an issue.

    If this is true, then perhaps it’s a legitimate time Managment and not a low interest level scenario. The girl also sounds like she wants to impress Oren, because she’s liked him for a year by suggesting a different venu. It’s too early to say she’s structured, I would give it one more shot (perhaps a Sunday funday brunch) and see where it goes.


    • Doc Love says:

      Hi Tony,

      Same answer I gave to Barry – women HELP you when they LIKE you – and telling a guy up front that there are all these “conditions” for the first date does not indicate someone he has a long-term chance with.

  • CORY WAGNER says:

    No one is calling out that this woman has a step-daughter? As in she is married to a guy who has a daughter? And the system is supposed to be the ultimate dating guide? Or is this supposed to be how to bed women regardless of their status?

    noun: step-daughter
    a daughter of one’s husband or wife by a previous marriage

    So now this system bullshit sounds like a huge scam. If someone needs the system, apparently they don’t know how to be human. Screenshotted what I see as the original post here so if it is changed I can post it later.

    Thanks! But no thanks.

  • Barry says:

    Hi Doc, I seem to always have schedule conflicts during your radio show so I figured I could ask it here. I’ve ran into very similar scenarios to Oren when the girl “seems” semi-interested but it’s very complicated to get a date with her. With the exception of the part where she didn’t like the restaurant, she did call back each time and countered the date immediately with 2 dates. If she didn’t call back and only texted, or didn’t counter with 2 dates, she would be out, but I was hoping you can elaborate on why this girl would be structured and a waste of time? Thanks Doc.

    • Doc Love says:

      Hi Barry,

      Remember what I always say, women HELP YOU when they LIKE YOU. Do you think she’d tell George Clooney (or whatever other star she thought was “hot”) that there are all these conditions for her going out? She’d JUMP at the chance to be with the guy – and that’s what I want for you guys. If they can’t make it easy to be with them then it’s a waste of time.

    • Ali says:

      Hi, can someone describe what structured woman is? I’m not english men and cant find any suitable translation for this. Thanks

  • Russ says:

    I agree, I was annoyed at Leila just reading this. She sounds very structured and there’s nothing worse than waiting around for a woman to get back to you to see if a date is on or off. I’m sure Oren can find other women at his dance events.

  • Barry says:

    Hi Doc. I’ve had a very similar experience to Oren before. My question is, on the surface to me it appears that she has high interest level – she calls back right away, she immediately counter offers with 2 dates. With the exception of the fact that she didn’t like the restaurant, if Oren had taken the 1st option that didn’t involve the step daughter, would she still spell trouble down the road?

    • Doc Love says:

      Hi Barry,

      It’s fool’s gold – she might call back right away but she has all these conditions like fine print in a contract – if she really had HIGH INTEREST LEVEL she wouldn’t take a chance of blowing it with the guy and wouldn’t put barriers in his way.

  • Denny says:

    Hi Doc,
    I read your Wednesday article every week and, before I read your answer, I try to do my own “System” analysis, then see how closely I come to what you say. In this case, I got the structure part right (i.e. she didn’t like the restaurant), but apparently I over-estimated her interest level. I tended to agree with Barry – she did a lot of things right initially (to her credit), but she seemed busy with a lot of things in her life. If Oren had taken the definite date, he would have expended a lot less effort, and it’s not her fault that he chose incorrectly. Is it possible that her interest level is above 50% and therefore worthy of one more shot by Oren? Maybe with a little “rule-setting” by Oren, she has possibilities.

    Always interested, Denny

    • Doc Love says:

      Hi Denny,

      I keep going back to the “conditions” she put on things – the maybe date on the one hand and then the “I have a time limit” on the other hand. Ask yourself if she would tell something like this to Justin Timberlake or George Clooney or any other guy she thought was super hot. Remember, women help you when they like you and her “help” was lukewarm at best.

      Thanks for writing!

      • NICK says:

        These time limits are nothing but low interest level. ‘ Ya il go out with him for like an hour to kill time cause after i have more important things to do’ Thats this girls mentality. NEXT Even when its easy its still not sure the interest is in the 90’s imagine when its hard. A similar situation is when they cut the date short every date. Another situation i called a girl to take her to an old port for dinner and a nice walk. Last second she is like ive been running arround all day im tired can we just stick to my area ? I told her its ok will make it some other time when your more energetic. She is like seriously ? Ya i’m serious. NEXT. Its like they don’t cancel but they don’t really want to come to the date either. Its as if they are being dragged.
        Stick to her area ? She should of been enthusiastic about where i’m taking her. All these scenarios are women with below 49% interest level.

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