August, 2026 | Doc Love - Dating Advice For Men - Part 5

Monthly Archives: August 2026

How Do I Ask Her Out While Others Are Watching?

DOC'S SYSTEM WAS CREATED BASED ON THOUSANDS OF INTERVIEWS WITH WOMEN - WHAT HE LEARNED FROM WOMEN IS TAUGHT TO YOU WEEKLY HERE.

In this week's post, Doc talks about just going for it if you are interested in her.  So important to do this and Doc will explain...

Dear Doc,

Yesterday I was in the checkout line at the local supermarket. The cashier who was ringing up my purchases was very attractive to me, probably about twenty-three or so. I’d seen her there before, but I’d never been at her particular counter before. While she was going through all my items, she was also asking me questions like do I live in the area and what did I do on my weekends for fun.

She was friendly but what I’m trying to say is that she seemed to be extra, extra friendly. She was really beaming such a radiant smile at me, and her eyes were so sparkly.

I wanted to ask her if she’d maybe like to go out with me some time, but I just wasn’t sure if she was romantically interested in me. I thought that she might have just finished some customer relations training where she’d been instructed to be super friendly to customers and that’s all it was.

The other problem was that there were other people in line behind me. I felt like even if I was sure that she was interested in me, how could I ask her out in front of all those other people.

So, there I was feeling all conflicted and uncomfortable and then she asked me what my name was. Now I’ve never had a checkout girl ask me what my name was. So, I thought, wow, maybe she really is interested in me, even though it just seemed too good of a thing to be true.

Then, as she was giving me my change, she looked at me with this sexy smile and kept maintaining intense eye contact with me. But I couldn’t linger any longer because there were other people waiting and I felt like it was now-or- never, do-or-die time. That’s when my heart started pounding.

I decided that I was going to act somehow and started to open my mouth to say something. I’m not sure what I was going to say, but before I could get a word out, the other customer in line started asking her questions about coupons or something so I just grabbed my shopping cart and started to leave. As I was walking away, she turned to me and said,” Bye.” Then I just said, “Bye,” back to her, and that was it.

Well, I’ve got to tell you that I felt really bad after that. I couldn’t stop thinking about her and what I should have done. But I’ve been comforting myself with the idea that I’ll be seeing her again. I may even go back to the market later today to get something that I don’t need yet just as an excuse to see her again. Hopefully she’ll be there.

So, what do you think Doc? What should I have done and what should I do now?

Delaney – who is kicking himself

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Hi Delaney.

Well guy, it’s obvious that you are a new reader, because if you had been studying “The System,” you would have known how and when to act in this situation. That girl was giving you more signals than a traffic light, and you should have ‘closed’ her before you left that market.

Yes, Delaney, you must begin to familiarize yourself with the concept of “closing.” That’s a sales term that means asking for the order, going for it, striking when the window of opportunity stands wide open in front of your face.

Now you mentioned that you were thinking about asking her if she’d “maybe like to go out” with you “sometime.” Even if you had said this to her, it’s a very weak, wishy - washy way to approach a woman. It’s not the kind of thing that a confident guy would say. Your choice of words makes you sound like you’re begging. Although, a weak “close” is better than no close at all. But you didn’t close at all, and now you’re suffering the consequences.

In future situations like this, you should ask yourself: “Which would I rather experience, a few moments of possible embarrassment or days and days of throbbing regret?”

Delaney, you don’t need to be sure if she’s interested in you before you “ask her out.” The way that you find out if she’s interested or not is by asking her for her phone number. When you take the direct approach and go for it boldly, you weed out the phony flirts from the ones who are sincere, and you move from confusion to certainty. Memorize these four magic words: “What’s your phone number.” Learn to use them whenever you can’t think of what to say.

Also, Delaney, never use the idea that you’ll see her again later as an excuse not to close. You must strike when the iron is hot. You may go back there to try to see her again only to discover that she has just left for a month-long vacation to Borneo or worse, she just quit and isn’t ever coming back. Whenever a woman is giving you positive buying signals, do not leave her without closing.

And when you told yourself that her liking you was probably too good to be true, you were mentally sabotaging yourself. You don’t think that a cool chick would like you. Get your self-esteem together. Expect good things for yourself. Think positive instead of negative.

Here’s another tip, Delaney. When you’re about to close and you find that you have an audience who will be watching as you put your ego on the line, do not be intimidated by them! You must go for it anyway. I don’t care if the entire noisy mob at the deli counter becomes strangely silent when you’re about to ask for her number. I don’t care if your heart is pounding harder than a ten-ton jackhammer. I don’t care if a news crew is broadcasting your conversation live on national TV. Close anyway! Life is short, and he who hesitates is lost!


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Who cares what other people think? You’re not there to get their approval. You’re there to get her phone number. You may crash and burn while several people are looking on. But rather than ridiculing you, more often than not, people tend to have admiration for you because you had the cajones to go for it. Other guys who might be watching will say to themselves: “Wow, I should have his kind of guts to go for it in situations like that.”

My recommendation to you is the following: As soon as you see your true love next, walk right up to her, smile and say, “Hi.” Then utter the four magic words. Badda bing, badda boom. Just like that. If she gives you the number, you’ll feel like a million bucks. If she doesn’t, at least you’ll be able to move on and get yourself out of Woulda' Coulda' Shoulda' Land.

Remember, guys, always ask for the phone number in spite of the crowds who are watching.

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