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Ask Dave-Dating A Bisexual Divorcee


The woman I'm seeing is going through a divorce and identifies herself as bisexual.

By Dave Singleton

ear Dave,
I was helping a friend of mine post a profile and ran across your column. I thought maybe you’d have advice for my situation. I met Annette at a local tournament and we became tennis partners for about a year and a half. I thought she was straight. We
She told me she was bisexual and made it clear that she was attracted to me.
never talked about our personal lives, but she knew I was seeing women and identified as a lesbian. Anyway, about six months ago, Annette told me she was separating from her husband and invited me to dinner. She’d requested the separation, her husband was upset, and he had just moved out two weeks prior. I figured it was probably going to be a night of girl talk. Instead it was one of the most romantic nights of my life.

She made dinner at her home, with candles and great food. I could tell she was feeling very shy when I arrived, and we ended up drinking lots of wine and talking all night. She told me she was bisexual and made it clear that she was attracted to me. I was taken aback, even though I was definitely attracted to her. Naturally, I was apprehensive since she said she was bisexual and I didn’t know if she was just interested in experimenting. I should add that I have been out for a decade, so being a lesbian isn’t new for me. Six months later, Annette and I are still seeing each other steadily.

This is her first same-sex relationship and I must say, there’s great passion on both sides. But though she says she loves me, she doesn’t identify herself as lesbian. Her divorce isn’t final, she hasn’t told people about our relationship, and I am worried that, despite her strong feelings, I am just a brief stop on her journey. I want more and am scared to tell her I love her. How should I approach her about becoming both open about us to her family and friends, as well as committed to our future together?
-Jill in Chicago

Dear Jill,
All relationships don’t run on the same timeline, but six months is a crucial juncture for many people. Chances are good that if you’ve made it to six months, you care about each other. But is that enough? She says she loves you and I can sense that you feel the same. But you are wise to be apprehensive. Annette is getting a divorce while having her first same-sex relationship. I am not sure which is more of a red flag:
  • The Marriage Breakup. You didn’t say how long she was married, but any breakup is bound to be traumatic. Like a horse at the gate waiting for the race to begin, she ran to your arms as soon as her separation was official. Even if she was hungry for a real connection with another woman, that didn’t allow time for healing, getting over guilt, or exploring dating options as a bisexual woman. Regardless of sexual orientation, breakups create a hurricane twister of feelings. Your relationship is in the eye of that hurricane.


  • First Same-Sex Relationship. Even if she’s felt attraction to women before, Annette is acting on it for the first time. In other words, she’s a newbie. It’s likely that her passionate feelings are at odds with shame and anxiety, and a shifting uncertainty over her identity in general.
While things are going well, you can’t cocoon forever. Eventually a relationship becomes an integrated part of your life. If it doesn’t, then it’s just a long-term fling—which might work for some people, but it doesn’t sound like it will work for you. You want the commitment and the integration of a romantic relationship.

The next step is to express this to Annette in as easygoing and introductory a manner as you can.
It isn’t cynical to acknowledge red flags in a new relationship.
There are big issues to discuss, but remember that it’s time for the first talk, not the ultimatum.

Find a time when the two of you are relaxed (don’t do this over the phone or in a letter) and tell her you are falling for her as much as she says she is falling for you. Acknowledge that you are in different places in your lives. But that doesn’t mean two people, over time, won’t find a happy middle ground.

Find out if she wants to pursue a healthy, real relationship. Define how you see that (i.e., your friends and family know you both, you don’t hide from the key people in your lives).

If she doesn’t want to pursue something more, then decide if you can be happy continuing this fling. If not, it might be best to end the relationship now before you get even more involved.

If she does want to pursue a relationship with you, then start talking about what’s essential to each of you, and agree to periodically evaluate how things are working. Think in terms of realistic progress. What does a good relationship look like at the one-year mark? What are some concrete goals for integration? An introduction to her family? A few dinners with your friends?

It isn’t cynical to acknowledge red flags in a new relationship. While true that excessive focus on a partner’s flaws keeps us from being happy with anyone, it’s important to differentiate what’s essential from what’s not. It sounds like your needs for integration and commitment are essential to you. After six months, it’s time to let her know that.


Dave Singleton, an award-winning writer and columnist for Match.com since 2003, is the author of two books on dating and relationships. Visit Dave’s website and send your dating questions and comments to him at davesingleton.writer@gmail.com.
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