Also make sure someone at home knows Exactly where you'll be. before I met my husband (online) my friend and I had safety questions. Any first date or meeting the friend waits an hour or so then texts a question only you can answer. then a few hours later do it again. if you're determined to stay in the same room (Highly recommend not) then at least have a friend do this several times throughout your stay. Personally I would say the heck with him, if he was really into you he wouldn't care where you stayed.

Save the small vacation apartment for your 10th meeting, your first meeting should be behind 3rd base at Yankee Stadium with a whole shitload of people watching. Give him a few dates to get a job and prove he can afford that 5 star hotel he craves.

I would strongly suggest you meet him the first few times in public around others, where people know where you are. I would suggest you don't stay alone together like in a bedroom to begin with as you have never actually met him. It is dangerous to meet him alone like that. You may love him, and he you, but there are too many situations where these things go horribly wrong. Please be careful and don't meet him alone to start with!

Hell no ... Follow what all the others said. If this is the first time you are meeting, you should keep it on neutral well public ground. And the whole unemployment and four star allure seems like a no go in the first place. I hope you are not so desperate, that you need to throw yourself into that much of a uncertain and possibly financially ruining relationship.

Run for the hills! As everyone has said, this is a huge red flag. You may feel that you know him well enough to call him your boyfriend even though you haven't met, but really there is no reason for you to stay in the same place together. If you do go ahead and meet him (I wouldn't, because when I see crazy coming I cross the street) you can just book your hotel, he books his, and you meet for dates like any other couple meeting for the first time. Don't rush into insta-pseudo-marriage with this idiot.

Why not get your own place near his hometown? Meet in a public place. After that request, I'd rethink spending the money.

You can never be too careful. Don't go blowing all your cash on him for your first meeting either. Don't know how long you two have been talking but some of these people online will keep up appearances for years just to get what they want in the end. I met my gf online 5 years ago and we talked for a year and a half before ever meeting. Still together so these things can and do work out. But a huge warning sign is already showing itself with that unreasonable 4star demand when you're the one footing the bill

lots of red flags, op. don't do it.

ding ding ding ding! that should be the sound of alarm bells ringing in your head!

Sooooooo many red flags, here. First, you've gotta be nuts to rent a room with someone you've never actually met before. Next, he's not working. BUT he expects YOU to pay for luxury accommodations. He sounds like a loser. You'd be smart to ditch him before it's too late.