She Sent Him A Book About Being Friends & He Still Pursued???

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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,

The girl of my affection is a secretary at the company I work for, where I’m one of the senior employees. Caitlin is 25 and I’m 32. We talked for the first time at a party. I had bought a new phone and she started playing around with it, using it to take pictures of me and the other guests. She said, “I see my phone number is missing from your address book. I’ll add it,” and then she typed in her number.

To me this indicated high Interest Level. But a couple days later I learned that Caitlin has a boyfriend. This confused me a bit, but I still proceeded to invite her on a date. While driving home afterwards, I made the big mistake of talking about one of my past relationships that ended in a “let’s just be friends” disaster. (I did not own “The System” at the time.) I’m sure this is what made Caitlin’s Interest Level drop very quickly. She then sent me a small book called Friendship. The next day I told her that I had to forget her. She said that “maybe” we could become more than friends in the future. I mostly ignored her from then on.

A couple months later Caitlin left her boyfriend. We started seeing each other again. Suddenly she was sending me all kinds of buying signals (holding my hand, visiting me in my office every day, looking for excuses to be with me more, etc.). We went out on a couple of dates that always ended nicely, but I did not go in for the kiss. I had a gut feeling that something wasn’t right, and that feeling stopped me from going in.

Two weeks ago, I went on a vacation to Africa. While I was away, Caitlin cared for my dog. She drove me to the airport and also picked me up when I returned (she had to take a day off to do that). Two days later, my best friend at work told me that Caitlin told him that she has a new boyfriend, another guy from our office, but that my friend was not to share this information with anyone. Of course she knew he’d tell me.

I know I won’t be able to avoid seeing Caitlin at the office. I’m confused all over again. Was it a mistake not to go in for the kiss? Was she waiting for me to kiss her? Or was she just playing with me, using me as a stopgap measure until something better -- a new boyfriend -- came along?

Hank - who’s back to collecting phone numbers

Have you checked out Doc's latest FREE video?  This week's subject is HOW DO YOU TELL IF SHE'S LOSING INTEREST? Check that video out and see what Doc had to say on the subject.

Hi Hank,

How can you say that one item – just one, single item – indicates high Interest Level? You need 60 items, guy! You can’t use just one buying signal, you need TONS of them.  

That said, it’s good that you got Caitlin out on a date despite the rumor of a boyfriend. Because you want to hear about this other guy directly from her lips. You don’t want to hear it from a stranger, or worse, from a blocker.

I’ve told you guys over and over NOT TO TALK ABOUT OTHER WOMEN OR PAST FAILED RELATIONSHIPS IN THE EARLY STAGES OF DATING. But since you didn’t own “The System” at the time, you’re off the hook. But pal, keep it in mind in the future – it’ll save you lots of anguish.

The real issue though, is not that your blabbing made Caitlin’s shaky Interest Level drop quickly -- it’s HOW FAR you made it drop. So this isn’t a good thing to do, my friend. How many times do you have to get your heart carved out before you stop spilling your guts?

Another problem with this scenario is that you’re putting yourself down. You’re telling this woman how you were such a loser that another girl had no choice but to dump you. And then she starts thinking, “Gee, I wonder if I’m going to have to do the same thing? Am I overrating this turkey? Maybe I should be dumping him.”

See, what you guys don’t realize is that when you put a little bee in a girl’s bonnet, she’s going to look at it, play with it, and attack it from 50,000 different angles.

Instead of the great hint Caitlin dropped when she gave you the little book called Friendship, she should have sent you the volume called Goodbye, Hank! Because she was definitely trying to tell you something, man. And then you go and tell her you have to forget her or you’ll die? The girl has a boyfriend, you’ve been out with her all of once or twice, and now you’re so tragically in love with her since she’s not available that you’re losing your grip. You can hardly stand to look at her anymore or your heart will break.   

Really?

But not to worry. Caitlin is a gal with a heart. She said you might become more than friends in the future! Great! You know how I love definite maybes. And you know how well they work out!

But good for you that you tried to ignore Caitlin after she told you she only wanted to be friends. Too bad you didn’t keep ignoring her. When she dropped her boyfriend, you took her back too soon when she gave you a couple of buying signals. The bad part is that girls with Interest Level of 40% to 49% will do that. And remember, you were going back to her. What have I always said about going back to a girl? YOU CAN’T DO IT.

Now, on to your main question – whether or not you should have laid a kiss on Caitlin. Buddy, on the second date you go in for the kiss – all the time. No exceptions.

But your gut was right. It was telling you that this girl didn’t like you and that she was just wasting your time. But that doesn’t mean you still can’t kiss her. To you Psych majors, no one’s perfect.

It was very sweet of Caitlin to care for your mutt. But did you kiss her when you left the country? Did you kiss her when you got back? That’s what I want to know.  

Yes, it was a boo-boo not to go in for the kiss. On the other hand, Caitlin wasn’t waiting around for you to kiss her. She was just playing with you because you’re the boss. She was either waiting for a new boyfriend or a promotion.

Remember, guys: you can’t go back – ever.