Love Letters

Advice: Why was it so hard to converse with my ex-girlfriend?

The stuff I find interesting to discuss seemed to bore her to tears.

Submit your questions for Meredith here.

Q. Hi Meredith,

I’ve been out of a relationship for about a month now. My ex broke up with me over vague incompatibilities. I’ve been asking myself what I should be looking to get from a relationship, and from outside of it.

I would often share something I found interesting with her in hopes of sparking a discussion. But she never seemed to engage with me, wouldn’t ask questions or show any curiosity. This left me feeling like I was performing a monologue, so I would end up shutting myself up.


Is this type of stuff best left to discussions with friends? I’d chalk it up to just being part of her personality, but I feel this is a common problem I’ve had with dating. Do I have unrealistic expectations of conversation in a relationship?

– Curiously Confused

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A. You should be able to talk to your significant other about things that interest you. If it’s a challenge to engage with your partner about, well, anything, you’re in the wrong relationship.

Of course, if this is becoming a pattern, here are some questions to consider:

Are you always monologuing? If so, have you asked enough questions of the person who’s sharing your time? Think about how you engage your dates. How much have you focused on them?

Are these topics organic at all? It’s great to talk about some article you read or question you’re curious about, but sometimes conversation can come from what’s happening in the room. Like, the quality of the food you’re eating. Or the weather. Or the music. It can be nice to share an experience, instead of hearing about an issue.


What makes your dates tune out? I can talk about my love of vampire movies all day. But I try to save that talk for the three people in my life who care.

Are you comfortable with silence? Because sometimes quiet is good. There’s an intimacy that comes with being able to sit with someone and not talk at all. When in a lull, think about whether you can take a deep breath and enjoy.

– Meredith


If your ex-girlfriend isn’t interested in communicating with you, then you picked the wrong woman to be your girlfriend. HARRISBLACKWOODSTONE

I personally love learning new things through conversation. It is also very attractive to be around someone who is intelligent. Curious though: After or during your “monologue,” are you actually listening to someone’s point of view? WRANGLERJANE

If you’re using topics to “spark” conversations, you’re in the wrong relationship. People who find each other interesting and attractive rarely are at a loss for words with each other.


I come across people every few years who I call lecturers. It’s impossible to have a real conversation with them because to them every conversation is an opportunity to spew all their so-called knowledge at the listener. Don’t be that guy. GRETCHYNN

Meredith Goldstein’s novel “Chemistry Lessons” is now available. Column and comments are edited and reprinted from Send letters to