Hey T,
I reconnected with Chantelle, who I was friends with in college, this past summer at an alumni function, and I could instantly feel the vibe that she was into me. She kept touching me, saying I looked better now than in college 10 years ago, etc. We ran into one another a month later and she asked me to go to the next alumni function in a few weeks. Since I was kind of interested in her at that point, I showed up. Right away, she showed interest again, and when she found out that I wasn’t married, she became even more interested and touched me more. She had recently been divorced and had a young child. We ended up going to a few bars after the event, and she continually expressed her interest in me, calling me her man, saying we could do great things together, etc. We ended up kissing quite a bit and the night turned very romantic.

Afterward, we planned on meeting up again. Chantelle has some family members that are ill. One recently passed away, and she has a parent who’s dying, so it was tough for us to meet, but eventually we did, about 10 days later. That date went well, too. We made plans to get together again, but I was busy with my parents coming to visit, and she with her child and family illnesses. So we decided to get together once my folks left and both our schedules cleared up. But when I dropped her an email asking what her schedule was like, I got no answer. I let a few days go before dropping her a text message. Still no answer. Basically it became like pulling teeth to get her to respond. I decided to email her saying that I liked her, but was wondering what was up and what she was thinking. I asked her to just be honest with me. I finally got a response saying she was busy with her dad's illness, a busy work schedule and her child.

I emailed and texted Chantelle a few more times over the next two weeks before she finally responded that her dad’s illness has taken all of her time and that she was casually dating someone else, but that this dating wasn’t the reason for the cold treatment (I call BS on that one). She said that she wanted to remain friends and appreciated me being concerned about her. Now, what confuses me is that she was the one who initiated the interest, and was the one who expressed her feelings first, and only then did I show mine.

What’s my next move to win her back?

Ivo - who is really confused

Hi Ivo,
First of all, why did you wait a month to ask Chantelle out? If you were interested in her, why didn’t you ask her out right away like you were supposed to?

All of Chantelle’s touching was great. To you psych majors, when she touches you it’s a very powerful “go” sign. But you have to remember that you have to have a lot of time in with the girl, plus a lot of green flags like touching in order for it to mean something substantial.

Kissing Chantelle and getting very romantic with her at the end of the first night was a huge mistake. Like my cousin Sal “The Fish” Love says, “What you did was give away the store for free.” The key to dating is withholding, not giving, which you don’t know because you obviously don’t have my book. And that’s what most guys don’t understand in the beginning of a relationship.

Ivo, you don’t ask a girl what “her schedule is like.” You ask her out for a specific, individual time and day. For instance, Thursday, Italian food, 6 o’clock. Black and white. No gray areas. And she will or won’t accept it. You give her the date and then let her worry about her schedule.

When you sent Chantelle emails and dropped her text messages and she didn’t answer, it meant you were out. It’s that simple. When you get highly inconsistent behavior from a woman two minutes after she was coming on heavy, that’s another reason for not kissing her. And it’s not like pulling teeth to get her to respond, it’s pulling low interest level.
But you continued to bug Chantelle and told her that you liked her. This is called begging, my friend. Begging lowers Interest Level even further. Think about it: a girl doesn’t return your messages and then you tell her you like her. Like my cousin Fast Eddie Love from East L.A. says, “Why don’t you send her two dozen flowers and an engagement ring while you’re at it?”

Then you asked Chantelle to please be honest with you. Ivo, that’s the best and funniest thing I’ve ever heard in my life! Did you ever for a second think that she was going to tell you the truth? When she told you how busy she was with all the different things in her life, you should have said, “Hey, when you get un-busy, give me a call,” then written her off.

But you emailed Chantelle a few more times after all that. Like my cousin Uncle Jethro Love says, “My God, boy, you’re beatin’ this horse to death!” In other words, you have no concept whatsoever of letting females chase you, being a Challenge, and that she should be wondering what you’re doing with other women. None of that comes into play with you, Ivo. Like my cousin Rabbi Love says, “You’re just an open book!”

Now Chantelle is “casually” dating someone else. Her dad might be on his deathbed, but she sure found time to get out with another guy, didn’t she? But, hey, don’t take it personally, Ivo! On the other hand, it is true that this other guy isn’t the reason for her icy treatment of you. No, the reason she’s treating you cold is because she doesn’t dig you!

Don’t be confused by what happened. You gave away too much too soon, my friend. You can show your interest by your actions, but you should never verbalize them. When you told Chantelle that you liked her, you might just as well have ended it right there. You had just two dates in with this girl. You have no basis for a relationship with her after only two dates.

How do you win her back? You have to hit the lottery, dude!

Remember, guys: If she goes out with you twice and doesn’t want to see you again, it’s OK to date other people.