In the US, is it concerning when a "grown man" in his 30s or 40s and beyond still lives with roommates, when dating and trying to attract a mate? Is there an expectation that you should be displaying a certain lifestyle that will attract a partner, and if you're living with a bunch of roommates, you're failing to do that?

I believe that's not the case in many other countries in the world, but what about the US?

It depends on what you want to do with your life, and what kind of partner you want. Most people want to date someone with their own place, because most people want their own place. If you want to live in a communal living situation, you're not going to be very happy if you partner up with someone who wants their own place. Will you sacrifice communal living in order to gain a partner? Or will you look for a partner who is interested in communal living, even if that takes longer?

These conversations about how men have to change themselves in order to find a partner are funny to me, because the subtext is that partnering up is the most important thing you can achieve, and you should sacrifice your other interests in order to make yourself marketable to the largest pool of people, so you can find a partner as soon as possible. People mock the phrase "just be yourself" because there are some things (money, physical beauty) that most people are looking for, and if you achieve them it's easier to find a partner. But the flip side is, unless you enjoy putting in all the work to be rich and beautiful, having a partner won't make you happy. The phrase "just be yourself" is really saying that you shouldn't change yourself just to find a partner, because it will be a phyrric victory. Instead, you should be yourself, do the things that make you happy, and let that filter out all the people who would only be interested in your money or your beauty. (and to be clear, this is not an argument against self improvement - you should still seek to better yourself)

Especially in high cost areas like NY or SF, it’s completely normal for adults, even highly successful ones, to have roommates. I personally know plenty of men who had roommates up until they moved in with the person they would end up marrying.

In the cities I've lived, this is standard yes. For better or for worse, a man that isn't displaying capability to provide for himself is typically less attractive than one who is. Again, this is my experience. I'm not making an argument for or against.

The US is a huge and diverse country. People in it have diverse expectations.

It’s also going to depend on the location. Having roommates in a very high cost city is no big deal at all.

If "displaying a certain lifestyle" means the person gets to visit a much larger home (as there's more incomes), get surrounded with lots of friends (since it's a vibrant community in the house), who all have stock portfolios to retire early on because of it (since they're saving an extra $1k+ a month by sharing the better living situation), then you'll probably be be able to find someone who finds that more appealing than the alternative (a loner who's spare money gets burned up going to a landlord or mortgage bank interest payments). Alternatively, if you look at folks attracted to the "drowning in credit card debt, but leasing a brand new BMW, and downtown apartment" version of "displaying a certain lifestyle" then no, those people probably will be repelled. The dating pool is full of unique people of varying philosophy, intelligence, and wisdom.

Yes, it is financially concerning. You do not need to own a house, but you do need to show you are financially responsible enough to pay for rent, utilities, etc all by yourself.

I dunno - having some social proof that a person can actually live with other people successfully is also a helpful kind of indicator.

There are such things as intentional communities. I predict multi-adult households will make a comeback. The era of nuclear families is coming to an end. It takes a village to raise children.

Depends on the situation. Generally I would say yes but I also know of successful people who have roomates (and can thus afford larger and cooler accommodations) and those people can of course throw parties and potlucks easier.

If you live in a shithole by yourself obviously that's not going to be attractive

Maybe ask some actual women instead of random men in tech?

Absolutely. All else being equal, a man over the age of 30 without his own residence is basically undatable (as per unsaid expectations in the US).