James: For the most part, the guy should always pay. It's fine to offer—but anybody who knows me, or is a gentleman, the guy will not let you pay. If you are dating someone for a while though, let her pick up a breakfast or something if she offers. But for the most part, the guy should pay. But here's a Don't: Don't bring all your friends and expect me to pay for them.
Glamour: Has that seriously happened?
James: Oh, yeah. Like, "Hey, let's go out for drinks," and then they bring their roommate and a few friends. They just expect...
Glamour: If I was going on a date with you, there is no way I would invite others to come along. I mean, I'd just want you to myself. That's just common sense!
James: See, those are the girls that are closer to my age and [maybe not mature enough]. Another Don't: Do not get on your phone and check Instagram in the middle of a date. That means you're more interested in what your other friends are doing than this conversation right now, and that will make me uninterested.
Glamour: Let's say you go on a great date. Should the girl text you afterward to thank you?
James: Of course text! Sometimes, because I am so busy, days will go by, and I'm not even aware of how many days it has been. Girls will read into that. Guys won't. If you want to text and say you had a great time, do it! Once again, if you're going to expect to have a relationship with somebody, and you're going to start off being noncommunicative, you're already going downhill. That's the most important thing in a relationship!
Glamour: What scares you the most about dating?
James: Ideally I'd like to find the person I want [to marry] when I'm closer to 30, so what scares me about going on a date with a person I really like, is "What if they are that person now and I'm not ready?" That's a scary thing. In the back of your head, you're thinking, Could I have a family with this person? If the answer is yes, then it's like, "Sh*t, what do I do?" Do you just keep staying in a relationship forever and ever, but will you be resentful at some point? Or do you break up and not enjoy what could be great? That's something I can't answer.
Glamour: How do your buddies know if you're really into a girl?
James: When they meet her more than once. [Laughs] When I don't like somebody, I don't keep them around. That's not to sound mean, but I don't have a ton of time [to waste].
Glamour: And how do you know when you really like someone?
James: I'm a pretty healthy eater, but I know I'm into a girl when I'm going out to get ice cream or have sweets with her. I don't have much of a sweet tooth, so that's how I know!
