In my three years as a single, I’ve learned that if I’m going get past the first few dates and actually start seeing someone, the next big milestone happens around six months. This is the point at which it’s clear, that while we get along, there are bigger questions to ask, like: “How closely does this person fit with what I think I want?” and “Do I know enough about this person’s strengths and weaknesses to really see him/her as they really are (in other words, without all that New Relationship Energy (NRE)? And “Do we fit together in a way that’s positive and enhancing for us both?”
These questions are hard, especially when hanging out together can be so pleasant, but they’re necessary if you’re considering taking your relationship to a deeper level. And if you don’t ask them, they don’t get answered.
For my friend Malcolm* a 40-something VC, the toughest question he had to ask Marissa, his girlfriend of six months, was why she was so resistant to learning more about his work. “It’s important to me that my partner know a lot about what do, so when I talk about work, she has some context,” Malcolm explained. “Marissa’s made no effort to do that with me, and I resented it. Finally, I just came out and asked her why she hadn’t made a greater effort, especially since I’d made an effort to learn more about her medical career (she’s an emergency room physician). She said that she didn’t think it was her responsibility to take care of my feelings related to the office, so we had a huge fight.” Now, three weeks after a brief break-up, Marissa and Malcolm are back together and having active discussion about how supporting one another’s professional lives fit into their dating and emotional life.
Letty, another friend of mine, spend six months dating Chuck, a former Zen Buddhist monk. They had a great time going to sustainability conferences, planning future co-housing, and just hanging out, but as the time went by, some serious questions about shared values emerged. “Chuck felt that a lot of my life was frivolous,” said Letty. “Working as a party planner and an event organizer seemed silly to him, even though I focused on green companies and local, organic suppliers. I realized I was dating someone, who, while he was very nice, basically just didn’t approve of me, and was getting kind of judgmental about it,” Although Chuck was open to discussing his values—and how he expressed them around Letty—she finally broke things off with him because the tensions between his values and her lifestyle became untenable.
“I found myself editing and censoring,”Letty says. “And I knew, right away, that if I had to hold myself back from saying what I thought to be dating someone, we just weren’t the right combination. It’s too bad, too, because in so many ways, Chuck seemed to be exactly the person I wanted.”
In my own relationship with A, whom I’ve been seeing for a little more than six months, the questions have been flowing fast and furious. We’ve discussed everything from political values to community consciousness, social mores to what we want in a life partner, and how we each measure/don’t measure up to those values. We’ve also talked—very carefully—about past partners—and where they currently fit into our emotional lives—not only in the real world, but in that emotional constellation called Who you still love, and why (and how does it make you feel?)
In all the discussions, some of the most helpful talks we’ve had had centered on the following topics:
- How do you see this relationship fitting into your life?
- How does that match—or not match—what you envisioned for yourself before we got involved?
- How has that original vision shifted—or not—since we’ve been together?
- Does this relationship feel like something you want to continue for a while?
- If yes, why?
- How
