Ask Wendy

How Do I Talk to My Boyfriend About Cohabitating?

Friday, October 18, 2019
Hey Wendy,

I've been dating my boyfriend for 18 months. He has his place and I have mine. We both have strong feelings for each and other, and I would like to know at what time do I ask about cohabitating?

We both do our thing, but more and bigger things can happen if we put our resources together. How do I go about asking that question?

Bessie S

Hey Bessie,

Congratulations on a happy relationship! Your question makes a lot of sense, especially in a culture that heavily promotes the relationship escalator: You two jump on (hopefully at the same time) and then it’s a smooth ride on up through dating courtship, moving in together, getting married or otherwise committing to each other long-term, having children (or not), and onwards into happily ever after. Sometimes, though, we need to get off this escalator to examine exactly what makes the most sense for a happy life—and not just any happy life, but specifically yours and your partner’s.

I couldn’t get a read on whether he’s leaning toward wanting to move in together as well or if he’s happier to do his own thing housing-wise, so instead of answering the question of “what time and how do I ask about living together,” I’ll guide you through a different kind of conversation. One where everyone’s needs and desires are considered, no matter where you both are on your relationship escalator ride.

I already have your preference: You’d like to pool resources, live together, and have a bigger life than you can have individually. Cool. But what would your big, new life look like if you had it all your way?

  • Are you moving in with him? He you? New place altogether?
  • Rent? Buy? Buy a single-family home?
  • Buy a duplex and live side by side?

Sleep in the same bedroom? In separate bedrooms?

  • If you buy a home together, who will own it?
  • If one or both of you own property right now, who will sell?

This is such a great question, because the possibilities are endless. It’s also a potential Pandora’s box, in which each answer leads to even more questions. This is why having this conversation now is probably the way to go.

Your guy may be excited to move in with you, and to all the things that entails: snuggling up next to you in the same bed, hanging out together in your shared living room watching TV or reading, brushing your teeth side by side in the mornings. Or, there’s a chance that he thinks his life is pretty perfect exactly how it is right now.

Eighteen months is a good amount of time to get to know each other and to get a feel for compatibilities, so you can arrange to have this conversation now. But instead of leading with “Do you?” or “Don’t you?” why don’t you two each take a turn at answering these questions one at a time:

“If I had it all my way, I would want our future relationship to look like ______.”

(State what’s important to you, what your deal-breakers are, and what would delight you to provide and to receive.)

“If I had it all my way, our living situation would be _______.”

(Be as specific as possible, and use my questions above for inspiration if need be!)

If you decide that you two are not going to cohabitate, then answer this question before you wrap up:

“The thing I most appreciate about our relationship is _______.”

If you do decide to live together, then ask each other these follow-up questions:

“Before we live together, what I want you to know about me is _______.”

(For example: What does alone time look like for you and how much of it do you need?)

“When we live together, if I had it all my way, we’d check in with each other by _______.”

(Text, phone, Google calendar, not at all. How many minutes/hours/days can you go without answering to each other about something? Just because you’re cohabitating doesn’t mean you own each other’s time. It’s important to not take each other’s time for granted and to set up best practices ahead of time.)

“The thing I worry about when it comes to living with you is _______.”

(Time to pony up your honest answer(s), here.”

“The thing I’m most excited about when it comes to living with you is _______.”

(This should be an easy one!)

Good luck, and happy communicating!

Do you have a dating, sex or relationship question for Wendy? Send it to Wendy@WendySpeaks.com.