(this is raw unedited text transcribed directly from the audio)
Here is the question about the guy who wants to ask a waitress but he knows that she has a boyfriend. I can feel for that, because we�ve all been attracted to people and we know that they�re �taken� and how do you deal with that situation?
�Hello Dr. Kenner. What insights can you offer the decorum of pursuing a woman who has a boyfriend? I am getting to know a waitress at a restaurant that I frequent on weekends and I find her attractive enough to want to know her more intimately. But, she has a boyfriend. My planned approach is to start talking to her about him and feel her out, to see where she stands with him.� Not a bad idea. �If she is serious with him, such as on the verge of engagement, of course I won�t bother. What exactly should I look for,� this is his second question, �as more subtle indicators that she may be ready to move on from him? Thank you, Larry.�
Larry, I am so glad that my husband pursued me, even when I had just broken up with a boyfriend but was on the verge of possibly going back with him or going back with another old boyfriend. I was in college at the time and my ex-boyfriend had been a really nice person, but even though I was dating him, I knew we had philosophical differences. I knew we had them. He tended more toward the mystical stuff and I wanted no mysticism in my life. So in the long run it never would have worked out, and I am a much better match, a phenomenal match, with my husband. So that�s my way of saying, man, give that waitress options! And you can give yourself options of letting her know that you�re interested in her. In one sense, you have absolutely nothing to lose. It may be a little embarrassing, may be an awkward moment, but I suspect if she�s like most decent women, she will enjoy your open expression of admiration and attraction and interest in her. Even if she doesn�t reciprocate or even if she likes her boyfriend very much, thank you, and lets you know that.
The next policy, the next piece of advice I want to give is, my husband dated a lot before we met. I did also, but he had this wonderful policy that helped him in the self-esteem realm. He wasn�t afraid of being rejected. He had a sentence that he said to himself � nothing ventured, nothing gained. That was it. When women rejected him he was like, �Oh well. I tried that and I�ll ask another woman out.� And so he was able to date many women over the years and that really worked out well for both of us because it isn�t like we got married out of high school and had never dated and didn�t know what our options were. We know we selected each other from a range of options. We had met a lot of people and had done a lot of thinking and we are each other�s wonderful choice.
I think it�s totally fine to approach the waitress and to say something along the lines � you�ll find your own words of course � I wish you weren�t dating. Let�s give her a name, Mary. �Mary, I wish you weren�t dating. I�d love to take you out for coffee or lunch sometime so you can be waited on. I enjoy your company. I enjoy chatting.� Now, I would not mention dinner right away, because women sometimes feel some pressure for sex � you take them out for dinner, pay, you�re there for a long time, you invest maybe $50 in steak and wine, and then it�s just awkward. I think the beginning dates, just starting something with coffee and lunch are better. Or you could say something else. You could say something along the lines of, �Mary, I know you�re dating Joe and I�m really curious about your relationships because I want to get to know you better. I don�t want to interfere if you guys are happy together, but it may be hard to keep me away.� Now, you�ve got to say this with a smile otherwise she�ll think you�re a stalker. Now, she may say, �You know, Larry, I am happily dating.� However, in private, she may reconsider her relationship with her boyfriend. Maybe there are some problems, like I had, and she would reconsider and you may be on the top of the list. I would say go for it.
You asked what are some subtle indicators that she may be ready to move on from the boyfriend? Well, one, if she talks about the boyfriend or you see him come into the shop and there are some negatives. We all pick up immediately the emotional cues we see with one another. Also, watch her body language and her tone of voice with you. Does she seem interested? Is she giving you a little bit of the flirtatiousness that goes beyond just being a waitress? We all know those subtle cues and I think if you sat down and named them to yourself, you�d do fairly well.
I�m Dr. Ellen Kenner on The Rational Basis of Happiness.