I want to talk about the important stuff

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Hi Meredith,

I'm restarting a relationship with my recent ex. We both expressed wanting to feel more seen and heard by the other person, and just communicate more often in general. We also felt that the first time around, we did a lot of going through the motions of dating and doing what we thought the other person wanted without really taking the time to listen and connect.

After about four months of not dating but still seeing each other as friends, we got into a conversation about what really happened between us and where the real disconnect was. During that conversation, I felt like I was introduced to a totally new dimension of this person and felt so grateful and so in love. Now we're back together, and I'm trying to find ways that we can open up to one another more regularly and understand each other better moving forward. Our time together is mostly really fun and sweet, and it can feel like a mood killer to bring up things that feel hard, but I know the hard stuff is super important. Any suggestions on how to incorporate more honest conversations about the darker things into our hangouts which are often filled with a ton of laughter and tenderness? Does a weekly "how do you really feel" check-in make sense? Or is that too structured? Do people actually do that? Are there ways to get deeper that don't feel like you're trying to be the other person's therapist?

– Getting Real


I think you should take it easy on yourself – and this other person. You just got back together, so this is Honeymoon Period No. 2. Allow yourself to focus on the positive, feel smitten, see stars, etc. Do not schedule check-ins right now. Do not force deep conversations.

That said, this letter reminds me of that New York Times Modern Love essay "To Fall in Love With Anyone, Do This," which is about a list of questions that are designed to help people bond. Writer Mandy Len Catron – who turned the essay into a book – asked this specific series of questions on a date and wound up falling with the man and committing. Questions from the list/essay include, "What would constitute a 'perfect' day for you?" and "When did you last cry in front of another person? By yourself?"

I know of some people who used other versions of these questions – some in the form of card games – on FaceTime dates during COVID lockdown. It was a way to bond. Something to do.

The questions – at least the ones that Catron used – are, in my opinion, designed to bring out the best in someone, and to draw out stories of vulnerability. They're also designed to get people to notice each other's strengths. I guess that's why my advice is to do one of these question lists as a game (I recommend the real one from Mandy's story), and instead of framing it as, "We must talk about hard things!," call it something to do on a cold-weather night. Maybe turn it into a drinking game (or some kind of game), where you try to guess each other's answers.

In general, remember that bonding isn't just about huge questions and tragedy. It's also about the fun stuff. So have some fun.

– Meredith

Readers? Ideas for sharing without making it feel like homework?