Dear Paulette,

A former coworker, who I was close to for two years, got a divorce six months ago. The marriage was always a disaster, but he had a hard time extricating himself. He has asked to see me many times via Facebook, and says he misses me. I was in a relationship too when we were work buddies who definitely had a strong connection. I finally met up with him yesterday (he lost a bunch of weight and went from hot to smoking hot). Because he knows me as friend first, and has seen me through the worst of days, I felt at ease… except, I think I’m in love and always was – just suppressed.

The problem is that he just broke up with someone he’s still in love with three weeks ago after a four-month relationship. He wants to spend time with me, but I think just as friends (though I felt an attraction years back). I can already see a future though!

Am I a transition? His marriage was always a disaster and he didn’t love the wife, but she is a difficult person and they have kids. This doesn’t feel like a not-over-her thing, but rather a not-over-the-next-girl thing. Ugh. Worse than this, this other girl he’s sad about is NOT for him! And I say this as a friend. I’m definitely this guy’s girl and am really hoping for him to get it.

Any suggestions?


Dear Dater,

First, let me say that I don’t know you or him, so you may be right that you’re a match made in heaven… if he’d just realize it! But since I can’t advise you on that, I’ll speak to the general issues that might be good to consider for someone in this situation. Here are at least 6 questions to ask yourself:

1.  Does he just want to be friends?

I heard you say that you were former co-workers and friends for two years, and that recently he wanted to spend time with you, but you thought that it was platonic. Some people say it’s hard to go from being friends to something more romantic, while others say a good friendship is the foundation of any great relationship. What do you think? The only way you’ll know if he wants more is to see whether he expresses a romantic interest in you, or by asking him. Some women do something in the middle by flirting a bit to show interest and then watching how he reacts.

2.  Am I a transition person?

People speak about being a ‘transition person’ or rebound when a person chooses to date them right on the heels of another significant relationship. Perhaps this is based on the assumption that people need time to heal and reflect before being ready to have another significant relationship. Although there are no rules about this, it generally is a good idea to spend a little time alone, reflecting and learning any relevant lessons from your last serious relationship, lest you repeat the same issues in the next one. This is why some people wait awhile to date someone who just got a divorce if they want it to be a serious long-term relationship.

3.  Is this good timing?

Timing often plays a part in relationships. Common conditions for successful relationships include an emotional readiness for intimacy and trust, a willingness to commit again, a desire to work on oneself and the relationship, an ability to be self-reflective, a capacity to learn from the past, and the awareness to resolve your past baggage so you can be fully ready to share your life. How might timing affect this situation? Well, if he just got a divorce from a painful marriage six months ago, and then broke up from a four-month relationship, who knows if he is ready to jump into another one? Or (if he is) if that is wise. Ultimately, that is up to the two of you, but it’s something I’d recommend thinking about.

4.  Does he have some challenging relationship patterns?

My first book, Dating From the Inside Out, is about how most of us have unconscious dating patterns around the type of partners that we continually choose. Unless we make these patterns conscious, we keep getting the same unhappy endings. I say this because you mentioned that he married a difficult woman and had a hard time leaving, and then was with a woman for four months who you said wasn’t right for him. He may be playing a part in choosing these types of relationships and may need to do some self-reflection work about what he’d like to create, in order to break his pattern. For example, I sometimes find that if a man had a controlling mother he may unconsciously choose more controlling women as partners. You may be great, but if you are more passive and flexible, he may put you in the friend zone and not feel an attraction. There’s little you can do about this unless he decides to date more consciously.

5.  Why do you already see a future with this man?

I find that when we feel ‘in love’ with someone, we often project all kinds of idealized things onto them. They could be a great person, but – objectively speaking – not a great romantic partner. I would recommend you step back and discern why you two would be a great match. Are your visions the same? Your values? How would you complement each other? Does he have the top seven things you want in a mate? Of course you’d need to meet his criteria too and there would need to be a mutual chemistry and commitment level. But my point is, don’t just go on attraction and fantasy, try to really think about what a long-term relationship with that person would be like. Then (if possible) you will see whether those feelings bear out in reality when you date.

6.  Should I tell him how I really feel?

After reflecting on these questions, if you still want to proceed, you may want to tell him how you feel. If you choose to do this, you may risk rejection, having your friendship become weird, or bringing it up at a time when he is only focused on getting over his breakup. On the positive side, you can only do your part in relationships by expressing yourself honestly and being willing to be authentic. So, if you choose to let him know you like him later (despite the above considerations), at least you know that you tried.

Dr. Paulette Kouffman Sherman is a psychologist and the author of “Dating from the Inside Out” and “When Mars Women Date.” She has a private practice in Manhattan and does dating coaching by phone. Learn more at and
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