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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).

Hey Doc,

About six months ago I asked out Kianna, a waitress at my neighborhood bar. She really stood out: very attractive, smiles a lot, and in her 30s (I’m 33, by the way, so we’re in the same age range). She informed me that she had just left a nine-year relationship but would like to date. She also told me she liked that I was so direct.

So we went on that first date, it was great and we both had fun! Then I was laid off from my job the very next day. I told Kianna, and while she said it didn’t matter, we only talked on the phone for a few weeks afterwards instead of getting together. This was because she didn’t accept any of my date invitations. So I backed off in hopes she would call me, but she didn’t. A month later she texted me a birthday greeting. I waited a week and decided to call her. Again, it went well. We started seeing each other on weekends, and dated for two months. During this time, we had fun, but beyond kissing, it didn’t get romantic. She told me she “couldn’t be a girlfriend to me now.” So I drove her home and left her alone. Three days later she called me, told me “I was the greatest guy ever,” and we went out again.

The next time I called her we had a nice talk, but it was different. She sounded distant. Well, being one to get to the point, I asked her out and she turned me down. I said “It doesn’t seem as though you are interested in this anymore.” After a short conversation about her wanting “to do other things, and go out and have single fun, but remain friends,” I said that wouldn’t work for me. We met for dinner to exchange our stuff, and she said she’d call me again. But she hasn’t.

Months have passed and my friends are telling me to call her again. I have a job again, and I’m sure my mood and demeanor are better. Maybe some time apart has helped her too. What’s stopping me is that if Kianna was interested, I feel she would have contacted me by now. Yes, I broke it off with her, but the roller coaster ride was getting old, and I wanted her to know that being unemployed didn’t mean I was a pushover.

Your advice is appreciated, as I’m confused about what to do. Could it have just have been bad timing the first time around? Or is no time the right time?

Chuckles - who doesn’t want to get burned again

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Hi Chuckles,

Well, I have to say that at the beginning it was good. Kianna helped you out when she met you. First she tells you she’d liked to date – implying of course that she’d like to date you. And second, she liked the fact that you were so direct, which showed you had Confidence - the first of the three Cs, the others being (Self) Control and Challenge. Straight out of the chute you did okay. So far so good.

But then you got laid off and went and TOLD Kianna about it. Why in the world would you tell her a NEGATIVE? To you Psych majors, telling a girl what’s wrong with you when you’ve just met her is about the stupidest thing you could do. Instead of flapping your lips, you should have just regarded yourself as “between careers” and kept your trap shut. Think about it this way: why would a girl like you more if you’re unemployed?  

What most men do is shoot off their mouths without thinking, and then they can never take it back. Remember, you can always tell her the bad stuff later.

Naturally, after your revelation about being stranded on the unemployment line, Kianna didn’t want to go out with you. She was turned off. And right there, pal, you were OUT. After she turned you down for a date, you should have thrown her number away.

But you waited for her to call you and she didn’t. Know why? Because SHE WASN’T INTERESTED.

She texted you a birthday greeting? Hallelujah! She saw the light! She realized what a great guy you were! Chuckles, you have to rush right back in there and try and get her back. What are you waiting for?

But seriously, it was a blunder when you decided to call her again. Sure, it went well the second time around – temporarily. It didn’t really go well, even though you dated for two months. And here’s the proof: it didn’t get romantic. That’s okay. Maybe this Kianna’s a classy girl.

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When she said she couldn’t be a girlfriend to you now, do you know what that really meant, Chuckles? That meant FOREVER. Guys, “NOW” is Womanese for FOREVER.

You didn’t really leave Kianna alone at that point. She was happy to get out of your car. But then you went out a third time when she suckered you in with that “greatest guy ever” comment. She must have been really bored at that point.  

I’ll let you in on something here, Chuckles. When females sound “distant,” that means you’re OUT. But you thought you were smart – you were going to be persistent, and you weren’t going to give up. As a result, the closest you’ve come to reality through this whole ordeal is when you told Kianna, “It doesn’t seem as though you are interested in this anymore.”

Kianna wanted to remain friends? Like the old saying goes, “Uh-oh, there goes the kissing!” Know what you should have done? You should have told her it was a great idea and then flushed her number.

But you had each other’s stuff. What stuff? How and why did you ever give this girl stuff? You weren’t going with this girl for two years, Chuckles -- you could hardly get a date out of her! And you’re giving her stuff?

Here’s another secret I’ll let you in on: when a woman says she’s going to call you again, it means she’s NEVER going to call you. More Womanese.

Of course your friends are urging you to go back for more – because your friends are even dumber than you are. Your mood and demeanor might be better now that you’re gainfully employed again, but it doesn’t matter. You’re out with this girl. Once Interest Level goes south of the border, it’s over, baby.

Regarding the break that was forced on you by Kianna, like the great Doctor Freud once said, “Time apart doesn’t help when they don’t like you. She’s just happy you’re gone.”

You really think that if Kianna liked you she would have contacted you by now? Brilliant! I never would have thought of that, Chuckles! You’re getting smarter.

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Dude, I got news for you: you didn’t break it off with this girl. To break it off with someone means they have to actually like you.

Being an unemployed pushover has nothing to do with Kianna’s Interest Level in you. And timing had nothing to do with this debacle either. You did everything wrong the first time around, that’s what really happened. This lady wanted to date someone, she liked that you were direct, she went out with you, but the problem was that only one of you had fun. And unfortunately for you, it wasn’t Kianna.

Remember, guys: there’s no such thing as bad timing.