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A Tale of Two Cities: L.A. vs Chicago, Which is Best to be Single In?

The spring is well upon us and temperatures are heating up. We may be on lock-down for now, but if you're single and have plans of starting over elsewhere in a few months, you might want to weigh your options depending on your dating prospects (among many other choices of course).

I've lived in Los Angeles for several years before moving to Chicago and despite being new to the windy city, I've come to notice a few differences between the cities that might make one just a bit more ideal for someone looking to mingle. As with most dating advice it is truly dependent upon what you’re looking to get out of relationship that will determine which dating practices are best for you.

Pros and Cons of Dating in L.A.

PROS: The Pickings Are Fine!

I suppose there’s something about living near the beach, cameras, and celebrities that rubs off on the common folk. Or perhaps all that sunshine, spirulina, and pH balanced water is doing the citizens of L.A. some good. Whatever the case is, the citizens of L.A. are some of the most attractive people in the U.S. Walking down the street can sometimes feel like an unintended catwalk.

Seriously, so many people there take pride in their appearance and it’ll make you want to do the same. I’ve lived in L.A. for several years, so I know that there are plenty of exceptions, but the general L.A. population is more attractive than the general population in some of the other states I’ve lived (2+ years in) in. Beautiful people congregate in this city and settle down.


One of the downsides to living in a city where appearance and stardom are a high priority for many of your neighbors is that the people there can be fairly self-absorbed and clique-ish. The men and women there are certainly a treat to look at, but having relationships that develop into any greater depth are difficult to attain.

I hear you, yes that’s true for most major cities, but L.A. takes it to a level that only New York can beat in terms of borderline narcissistic self-obsession. You might be competing with your man for the mirror and you’ll definitely be competing with your girl for the mirror. I’ve been more successful in making friends and dating people who have moved to L.A rather than the L.A. natives.

PRO: Open Minds

I guess having a yoga class on every corner and some of the chilliest garage band music has assisted in making L.A. on of the most open-minded places in America. If you want a partner that isn’t locked down with boring flat-minded ideas or who will impose restrictive narratives on you, then L.A. is the place. Both the men and women are more open to letting you just be yourself no matter how different that may be. You’re truly just an individual in this city and that’s all. If you’ve ever wanted to date someone from another culture L.A. makes it easy. Everyone’s open to exploring and there’s a place for you in other communities outside your own.


This is a potential con. I’ve noticed that most people want a partner that will see them as just a human being and accepts them flaws and all but will have trouble accepting someone else that falls outside the status quo. You’re going to have to practice being more open minded too. Your guy might have been interested or is still interested in seeing other men. The girl of your dreams used to be a stripper. L.A is full of interesting characters and you’re bound to be part of their story line at some point. Of course, it’s quite easy to stick to just your circle in that city but L.A. has a way of throwing everyone in for a loop.

The Pros and Cons of Dating In Chicago

PRO: Romance

I’m not sure if this is just my unique experience or if it’s common enough to be a thing, but perhaps the millions of art institutes have made the people of this city charmers. The people of L.A. are charming too but it’s incredibly phony. Though, In Chicago the gestures at least appear more genuine if they aren’t actually more genuine. The men and women of Chicago are a lot more down to earth despite living in the city. They say Italians are romantic and everybody and their cousin are Italian over here so accept that dinner date to Maggiano’s and enjoy your night.


The people here might be a bit more traditional in their lifestyles. At first it may appear refreshing but running into zealots of different communities becomes depressing. You’re less of an individual in this city than you are in L.A. but your tribe is definitely out here somewhere.

PRO: Greater Sense of Community

Chicagoans are definitely more community minded. Everything is inherently better when it’s around them and so are you… if you’re in their area. There was an article written on what makes Chicago’s dating scene unique and I’ve come to find it true. You can be talking to a guy and things will look like they’re heating up, then he asks where you stay and suddenly the conversation becomes more neutral until it fizzles out.

Due to their more communal mindset, the city has more of a small town feel which can make it feel more homey than other larger cities. And while Chicago might be one of the top 3 cities to use tender It’s been my experience that you have a far greater chance of making genuine connection with people than you do in L.A. Commitment is actually a thing over here.


If you’ve ever been to L.A. you’ll know that the neighborhoods are certainly separated but not like how they are in Chicago. If you’re someone who prefers sticking to your own roots, then the Chicago scene makes it easy but at the expense of exploration. Chicago neighborhoods are highly segregated and completely different than L.A.’s more lax cultural mixing pot. Chicago has a lot to offer in terms of cultural exploration, but you’ll need to make a much greater effort than you would in L.A. People prefer to stick to what they know all across the country, but it’s more pronounced in Chicago than it is in L.A.

Honestly, both cities are amazing and offer their own romantic adventures. L.A. is more friendly to the unorthodox and Chicago is that home away form home. I'm still getting a feel for Chicago and so far, I've been liking the dating scene here. While I may have addressed over-arching themes for both cities, each has something to offer everyone.

Lilith is a blogger with an emphasis in writing and reflecting upon social agendas that effect black women. When not at her computer writing she is more than likely still at her computer, programming. On the rare occasion that Lilith isn't at her laptop you can attempt to find her exploring the Chicago food scene or attending workshops in creative writing

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