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Dating a City

Does It Feel Like Home?

The number of people looking to relocate today is massive. Thirty million U.S. citizens move each year and eight million more* plan to move due to new work-from-home policies. 

You can do all the online homework in the world but ultimately you're still going to ask yourself: do I want to for sure want to live there? Could it feel like home? How can I figure that out? Well, it's not so different from the step (s) you take in deciding whether you want to marry someone. And it starts with dating.

Our site, LookyLOO, offers suggestions for how you can “date a city” so you can feel comfortable making the move or moving on. Here are several of them.

CANVASSING A NEW NEIGHBORHOOD

  1. If at all possible, take the opportunity to experience the cities of interest for a couple of days - including at least one weekday. Don't make the mistake of going only on days when the city is busier than it might be on a normal day in the life. As someone who made the mistake of visiting and buying a house on a sunny day, in the fog belt of San Francisco, make sure you visit on a day or days that fit the profile of the typical day in the city.
  2. Avoid chain hotels and stay at an Airbnb or VRBO or the like. It forces you to wake up, walk, take public transport, drive, and live in what might be your new neighborhood. Maybe you can fake it with a B&B that's embedded in the neighborhood if Airbnb or VRBO's are unavailable.

GET UP EARLY

  1. Cities reveal some of their best and worst attributes early in the morning. What would a real-life commute look like for you? What about access to and ease and cost of public transportation? How close is the airport? Is anyone riding bikes? Walkability? How busy are the coffee shops and breakfast spots? Is there parking? Are Uber and Lyft readily available? What intractable challenges appear? 
  2. Of course, in some resort or retirement cities, it’s not as busy early in the day. “Rush” hour in these places might be mid-day. Again, make choices about your behavior when visiting based on what you'd normally do. Don't just be a tourist when you're in "dating" mode.

STAY UP LATE

  1. Or at least later. Do the sidewalks roll up at 9:00 pm? Is that good or bad? What kind of nightlife does the city offer? Who do you see in the city? What about entertainment? How close are your preferred sports venues?

ENGAGE EVERYONE

  1. Most people you meet love to converse and help – and they have most of the answers. Ask away. Why do they live and work where they do? Why do they stay? Why should someone like you relocate to this community? Why this city vs. another? You’ll hear all the positives. You’ll also uncover the drawbacks to living there from those who know it best. What’s the underbelly? In addition, you’ll get an opportunity to delve into the specifics of the things you care about. These conversations also reveal tips and tricks – perhaps learning about free admission days to museums, how good the weekly farmer’s market is, finding out about the nationally renowned senior center, amazing festivals, and the address of the best vegan restaurant. You might also discover how to avoid the lines to just about anywhere you’re going during your stay.

UNCOVER THE CULTURE

  1. These conversations, along with your people-watching skills and the conversations you overhear, will begin to reveal a culture. What are the people like? How do they treat you and one another? What do they and the community seem to value? How do those values sync with your values? What’s the vibe? Does it give you energy? Do people seem happy? Is anybody laughing? What did you learn during your visits? Did you want to linger? Can you picture yourself here? Does the idea of moving here excite you? How did it make you feel?

As LookyLOO recommends, “dating” the cities on your shortlist will be well worth your time as you discover the next great place to call home. 

*Source for the annual number of movers in the U.S. data: Zillow 2020 Market Report