He takes you on nondrinking dates. Nothing wrong with a few cocktails on dates, whether you’ve been out twice or for 20 years. But the beginning of a relationship tends to be pretty socially lubricated, so when he starts asking you to hang out in broad daylight without a beer, he’s getting comfortable with you.
He expects that you have plans even when you don’t make them. In the beginning, he asks, “What are your plans for this weekend?” to see if you’re available. When he’s serious, he asks, “What are our plans for this weekend?” because he just assumes you’ll want to be together.
He brings you along to his regular activities. Taking you to a big deal event like a wedding is, of course, an important sign in its own right. But for stuff like that, people expect him to bring a date, and plus, that’s only for one night. On the other hand, if he’s bringing you to a usual thing he does frequently, like to his weekly Sunday-night dinners with his friends, he’s doing it because he wants to and because he plans to have you around for a long time.
He talks about you when you’re not there. Especially to people who matter. “Once when we were first dating, my boyfriend mentioned off-handedly that he’d shown my picture to his parents,” says a friend of mine. Four years later, both he and his parents still love her.
He makes room for you and expects you to do the same. It might be a cliche since the time Carrie Bradshaw unsuccessfully tried to leave a hair-dryer at Big’s, but most guys seem to agree: If they’re intentionally leaving a toothbrush at your place or offering you drawer space at theirs, they mean business.
He lets you see how he actually acts with his friends. Introducing you to his friends is one big step, but those first few times, he’ll probably order them all to be on their best behavior. When they start acting like the loud, dorky, possibly obnoxious-at-times dudes they really are, even when you’re there, they all see you as a permanent fixture in his life who can handle the truth.
He stops trying to impress you quite as much. You certainly don’t want a guy who takes you for granted, but hear me out. A guy who’s always on his best behavior is still in the stages of trying to win you over. That stage is fun, but it doesn’t necessarily mean he’s sure about you. A secure guy will let you come over when his bed isn’t made or disagree with you about that movie you loved even if it makes you mad. If he still makes you feel special and loved but does so while letting you see that he’s just a regular human with bodily functions and a few bad habits, it’s because he thinks you’re the right one for the real him.