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(Editor's Note, this letter was written before Doc's death in August, 2020 but still relevant as Doc's principles are timeless).
Cherry is a designer I met through a mutual business contact. I am a tile setter and did a few jobs for her. She said she would like to get together for a drink or dinner and we did. At the end of the evening we hugged, and I said I’d like to take her out again.
I called her a week later and we made a date for a lunch and a museum. I was so nervous that my hands were shaking while we were eating. I’m not sure if Cherry noticed, but it seemed that she changed soon after that. At the end of the date she gave me a hug and I gave her three daisies. I waited five days, then called her and got her voicemail so I left a message about getting together on the weekend. I didn’t hear from her and let the weekend pass. On the following Tuesday I called again, and again I got her voicemail. I knew something was wrong, and thought back to my shaking hands. I said that I wouldn’t be mad at her if she had a change of heart but I did want her to understand that I didn’t want anything to happen to our growing friendship.
A few days later I got an e-mail from Cherry saying that her heart was not in a relationship but that she would like to continue the friendship. I then wrote back saying that I was sorry and that I was growing fond of her and felt bad that I made her have to write the letter in the first place.
I didn’t hear from her for a few weeks until she called wanting me to do a small tile-setting job for a client. Then she asked me to come to her home to pick out a paint color for her walls, and maybe we could go out together and pick up the paint. Now I’m getting really confused about what she wants. I know enough not to jump into anything too soon but how should I handle this? Is it possible that this is a second chance for me? I plan on just being myself and not looking for anything that isn’t there, but thanks for any advice you can give me to help my cause.
Wesley - who’s trying not to get his hopes up
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Why in the world are you telling this woman you want to take her out again? Putting aside the popular myth that women want guys who spill their guts, let’s suppose that Cherry wants a man who plays it cool and would rather drag his interest out of him. Well then, you blew it, pal. To boot, the goal is to try and read her Interest Level, and the way to do it is by not coming on heavy. To you Psych majors, if you come on like gangbusters you’re going to LOWER her Interest Level.
It’s okay that your hands shook when you were out with Cherry. I don’t know if you’ve memorized my material yet, but either way we’re going to help you. Let’s say you knew your hands were going to shake – that it’s happened before. Well, then, you should have done something else with this girl where she couldn’t see your hands shaking – like take her to an IMAX movie. Then do it for two or three dates until you get comfortable with her and your hands stop shaking.
But of course Cherry changed after she saw you doing Saint Vitus’s Dance. She looked over at you and saw you juggling, but she didn’t see no balls in the air! So why would she want to go out with you again?
But her lack of interest wasn’t stopping you, dude. You went ahead and presented her with a bouquet. Why are you giving this stranger flowers? We want her wondering how many women are chasing you, versus how many women are rejecting you because you’re needy and you come on too strong. How did you think this girl was going to interpret your mushy gesture? Remember, guys, unless it RAISES Interest Level, don’t do it.
But you weren’t finished. You called Cherry and left her a message. Why didn’t you just ask her to meet you at the jewelry store so you two could pick out the ring?
You didn’t really “let” the weekend pass, buddy. You act like this girl’s dying to see you. How can you say you “let” it pass? What are you trying to do, save face here? Come on, guy, don’t try and snow me -- I’ve been in sales all my life!
You knew something was wrong, all right, except that you thought it was Cherry’s voicemail that wasn’t working. But you insist that you two have a growing friendship. Guy, she doesn’t return phone calls! You call that a growing friendship? Wesley, please, you have to lay off the Gallo!
Now, dude, why would you tell someone who doesn’t want to have a romantic relationship with you that you want to have a relationship with her when she just told you she wasn’t interested? Like the great Doctor Freud once said, “Did you do it because you’re a great listener?”
YOU apologized for making HER write a letter? I can’t believe you, Wes. You’re giving me wimp chills!
But at least you’re going to get some money out of the deal even though Cherry rejected you. It’s great that she wants you to help her pick out her paint. If it were me, I would have asked her “By the way, when you make out the check, it’s 40 bucks an hour!”
But on the other hand, you’re getting a free dinner out of it. Look at it this way. Maybe Cherry wrote you off, but she likes your work. Consider the economics of it – she keeps giving you leads.
So stay on the business track, Wesley, and forget the romance. And by the way, how do you set tile when your hands are shaking?
But you’re still confused about what she wants. Dude, she doesn’t want to be with you. Her Interest Level in you is 1%. CORRECT. I said 1%.
You’re not about to jump into anything? My friend, you’ve been jumping around like a Tasmanian kangaroo! You think you’re getting a second chance? Yeah, and you’re going to win the Powerball drawing next week, too!
Wesley you’re out. Like the Reality Factor says, “What are her actions?” Hey, she doesn’t call you back!
But the good part is she’s getting you business and that’s the main thing here. You’re making dough off this woman. Usually when they drop you they won’t give you the time of day, but this one’s shooting you leads. The only down side is that maybe she’s looking for someone to paint her walls for free.
Remember, guys: the key to women is not charging in.
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