Flirting with the Unavailable


After fifteen years of marriage, I am back in the dating pool. I have known this gentleman for two years and he and I have flirted back and forth the whole time. He now has a girlfriend of one year, but never speaks positive of her. He still flirts a lot and at every opportunity either hugs me or holds my waist or hand. He got together with the girlfriend when he thought I was married (it was a long drawn out divorce). He knows the divorce is official and is always asking me things about my life. I asked him if he is going to get married and he said that he “isn’t giving her a ring just to make her happy.” He has told me once that he loved her, but wouldn’t look me in the face. I think about him constantly and this is the first time for me to ever be like this. I just don’t know how to read when a man flirts the way he has – is it in fun or is he trying to tell me something? And should I let him know my feelings or just let it ride?



There are a number of things for you to think about here. First, how long have you been “in the dating pool” again? It sounds like a very recent divorce and thus, after fifteen years of being involved with someone I would encourage you to step back, focus on your life, and getting a grip on “life after divorce” before you focus on trying to jump back into another relationship. When we are with someone for a long time, it is easy to lose ourselves. Often, we eat what they like, plan our days around their schedules, and invest a lot of time (especially just before the split) in trying to either save the marriage of draining a lot of energy in fighting. This can leave you feeling pretty empty—and needy.

It is much healthier to start new relationships from a place of peace and strength than from a needy place. When we are needy, we tend to settle for less than we deserve. For instance, pursuing a flirtatious, unavailable guy. You need to respect that he is in a relationship—whether he respects her, plans to marry her, loves her or not. He is in a relationship with her—for whatever reason. If he hits on you or asks you out, let him know that you are confused because you have feelings for him, but he is clearly not available. See what he says, maybe make a lighthearted joke about how your timing has been off and when the day comes that you are both available—yahoo, but until then, you can’t pursue this.

The reality is that you deserve a relationship with someone who is available, interested and honest. What you want to avoid, especially right as you are coming out of a long relationship, is getting involved with someone who cheats on his girlfriend and flirts incessantly with others.

When you start a relationship in which one or both of the partners are cheating on someone, trust becomes very difficult because you know they are/were capable of being dishonest.

I know it is hard to pull back and be sensible when you are excited about someone, but I want you to take a careful look at whether part of your thrill around this is because you have been starving for someone to flirt with you and make you feel special for the last ten years. Attention, especially after a long drawn out divorce, can feel really good. Be careful not to confuse, “I want to feel loved” with “I want to feel loved by him.”

I wish you the best,

With Aloha



Intellectual Foreplay Question of the Week: Does flirting count as “cheating”?


Love Tip of the Week: Flirting is a lot like fishing; it is setting the bait. Be sure you don’t use bait that is the favorite of the kind of fish you don’t want to catch.