1. What's your daily routine?

This line of questioning will be a slow burn. Start small by walking them through a typical day in the life. The goal is to get a feel for what a typical day for each of you is like sans drama or outside stressors (we'll get to those).

2. How would you prioritize the following activities: work, play, clean, and rest?

The priority placed on values themselves is more important than actually sharing values. For example, hyper-organized and messy individuals can happily cohabitate under the same roof if they both rank the priority of cleanliness on the same level.

The priority placed on values themselves is more important than actually sharing values.

3. Do you believe in past lives? If so, who were you in your last lifetime?

This technique is what Tony Robbins calls a pattern interrupt. Things are going to get personal, so jump in with a whimsical, fun line of discussion. Disrupting serious conversations with off-kilter, provocative questions will get you out of your shell. This is not a job interview. Odds are that this human is going to walk in on you in the shower within the next few weeks, so don't be afraid to break the ice.

4. What time do you generally wake up and go to bed? Early to bed, early to rise or night owl?

An important follow-up to this: Are you a light or heavy sleeper? The answer to this one will establish the nightly sound barrier of your home.

5. What conditions do you require to sleep?

If you're consistently up late and your roomie leaves for work at 5 a.m. (as is the case with my living situation), you need to set ground rules. Agree to only listen to music with headphones after a certain hour or promise to turn the lights off by a certain time.

6. What is the best means of approach to make a request?

Does your prospective roommate prefer to hash things out face to face, or is text appropriate? When I moved in with my roommate, we established a system. All complaints and requests were to be made in writing via text.

7. What do you use your home space for? Do you work from home?

Some individuals may merely use their home base as a launching pad for the day. Others might view their personal space as a sanctuary to regain their mental strength or a spot to entertain friends.

8. How neat or messy are you?

Some people may want every ounce of clutter removed from the premises. Others may be cool with keeping common areas spotless and allowing a contained explosion to occur in their own closet. Discuss what your policy is when it comes to cleaning up, and then work out if the solution is hiring a housekeeper or DIY.

9. If you could name one place that would sum up the vibe of your home, what would it be?

This can be a metaphor or a physical place, the point being: There is a big difference between NYC and Tahiti. If your idea of a homestead is an after-hours club and your roommate has more of an off-season resort energy in mind, maybe work that out before you come home to strangers dancing on your coffee table at 4 a.m.

10. What's your pet policy?

I rescued a dog within two months of moving in, and my roommate encouraged it. Inquire after any short- and long-term pet goals. Maybe it's a lifelong dream to own a Bengal cat, and they are waiting for the right moment. The last thing you want is to have to move out due to an allergy or aversion to change.

11. What are your biggest stressors in life?

It's helpful to know if you'll be living with someone who ranks their personal relationships at the top of their priority list. If work is number one, great. Life will bring the drama. Knowing where the minefields are will enable you to compassionately maneuver around red flags. Maybe cut them some slack during the busy season at work, etc.

It's helpful to know if you'll be living with someone who ranks their personal relationships at the top of their priority list.

12. How do you decompress day to day?

I am convinced that my roomie knows most of the secrets to life. One of those secrets is that he watches the puppy channel every day after work for a half-hour to decompress. I know he needs that half-hour, and it is sacred space. Love bubble baths?

13. One question most roommates forget to ask their roommate: Are you a vegan? Are you vegetarian? What is your policy on those two matters?

Check out the recent Redfin article iROOMit was featured in, where we talk about this question in more detail: 14 Top Tips for Living with Roommates: How to Find the Perfect Match

14. What are your feelings about overnight guests?

Make sure there aren't any steadfast rules or that you both agree if there are.

15. What's your worst habit?

Pat yourself on the back if you know what it is. If you don't, ask your previous roomie or your best friend. This is a growth opportunity for you, and it's a heads-up for your new roommate.

16. What chore do you least like doing around the house?

I'm a strong advocate for divisions of labor. If you hate doing dishes and your roomie hates cleaning the bathroom, why not settle on a quid pro quo? At the very least, if they know you hate doing something, you'll probably get a big thank you every time it gets done.