Ask Dave-She’s a single lesbian mom

After changing jobs, one woman has a chance to date her crush. The problem? Her crush has a son!

By Dave Singleton

ear Dave,
Last year I met a really gorgeous woman at work. For a very long time, I resisted having anything to do with her beyond small talk, even though there were obvious sparks between us. We worked on different floors, so all the flirtation would happen in the elevator, at company events, and the occasional hello in the parking lot. A few weeks ago, I got a
Having a few drinks certainly lowered our inhibitions and we finally made a connection.
job offer somewhere else and put in my notice. At my going-away party, she and I talked and, before I knew it, we ended up in bed together. Having a few drinks certainly lowered our inhibitions and we finally made a connection. I was ecstatic.

When she left the next morning, I asked her out the following weekend, happy that I was finally free to date this girl without work issues coming up. I was shocked to hear that she couldn’t see me because that’s her visitation time with her 10-year-old son! She had him really young; she and the father got engaged when she discovered she was pregnant just out of high school, but they split before he was born because she realized she was gay. I’m feeling very conflicted. I don’t know how I feel about dating a woman with a kid. This is a totally foreign situation to me. Also, I’ve had feelings for this woman for almost a year and had no idea about her son. Don’t you think it’s weird she never brought him up? Still, I can’t help but feel that all this happened for a reason; how should I approach this?
– Kid-phobic Katrina

Dear Kid Kat,
For single gay parents and those who date them, navigating the road between lovers and kids is a major stress, high on the list with other challenges such as coming out and legally protecting your rights as a gay parent. A lesbian friend of mine said once, “As I get older, I really appreciate low-maintenance women. You know the kind; no more than two cats, dead parents, and no kids.” Though she laughed when she said it, I am not sure she was joking.

You might feel the same. It sounds like you were surprised by her morning-after revelation.

But I’d cut her some slack for not telling you. You’re indignant, but why? What did she do wrong? A coworker you hardly knew didn’t share details of her personal life and you’re upset? You admit you avoided her, other than offering minimal small talk. Then after the sparks fly – and cocktails pour – you end up spending the night together. You found out about her son the next morning. It’s not like she was keeping him a state secret from her closest gal-pal, right?

In baggage terms, dating a single lesbian mom can be a heavy load.
I think what’s passing as indignation might be disguised fear. It’s daunting to date someone with kids, I understand that.

But if you’ve had feelings for this woman for such a long time, your attraction is strong, and (whew!), you are no longer coworkers (dating a coworker leads to a whole other host of complications), then why not explore it?

Just know what you might face. Using a work-related reference to illustrate my point, corporate mergers sometimes take months or years of effort. Why should merging a girlfriend and kids, which probably has more heated emotions attached to it, take less time? My advice is to keep your expectations in check.

In baggage terms, dating a single lesbian mom can be a heavy load. But there are ways you can you lighten it and minimize the conflicts if you ask the right questions first.

First, spend some time exploring your feelings about this surprising twist. As you note, this is totally foreign to you. We all arrive in new relationships as “package deals,” in one way or another, whether it’s through demanding parents, jobs, kids, or other life situations. Considering that a kid is part of her package, ask yourself if you want “the package?”

Before you move further into her life (and vice versa), make sure you are open to what that might entail. Let her know sooner rather than later whether you are willing to accept her package. Many parts of a relationship are negotiable, from sharing finances to who control the remote. But a person’s kids aren’t on the table. If you know you’re only interested in her alone, or if you don’t like kids, this is a huge red flag that you shouldn’t get more involved with her.

Second, once you’re clearer about your feelings about the combination package of her and her son, and assuming you want to pursue dating, focus on your questions for her. What are her feelings about dating, given her parental responsibilities? Has she done this before? What was that experience like and what did she learn from it? Is having a meaningful relationship one of her goals and, if so, how integrated does that look to her? Can she imagine bringing another woman into her and her child’s inner circle? As a single mom, what kind of relationship does she envision for herself?

Yes, it’s daunting in the first few dates to deal with anything heavier than where to eat and what movie to see. But with an issue so important – and so nonnegotiable as a child – the sooner you explore this together, the better.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at
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