Colbert, who has three children of his own (including an 18-year-old daughter), expertly fielded questions on misogynist jokes, boyfriend-based dilemmas, and how to tell if someone thinks you're cool.
"I'm honored to be considered a grown man," Colbert opened his video by saying, before going on to answer four questions in the 10-minute vlog.
Check out the four fan questions below and Colbert's advice (out of character!) on how to handle relationship problems:
1. "I know most men aren't jerks, but when guys - especially teenage guys - do stuff like cat call and make jokes about rape, do they know their behavior is harmful? Is that why they do stuff like that or is it because society has taught them to be misogynistic?" - Loretta, age 14
"I think, Loretta, that the reason boys do this kind of stuff is to get your attention. And no, I don't think they mean to be harmful because I don't think they know that it's harmful. I think they just desperately want you to pay attention to them. So, my advice would be, if you don't know the person doing it then try to ignore it. If you know the person, they really care what you think - it may not seem like they do because they're being so aggressive, but they really do, so I would say, 'Please don't do that, I really don't like it.'" They may blow you off at the time, but I promise you they will remember you said that and for this sort of thing to stop, boys need to be educated.
Does our society educate boys to be misogynistic? It probably doesn't value girls and women as much as it should, and boys probably see that as a signal that they can get away with things like devaluing women."
2. "My dad won't let me sleep at my boyfriend's house and there's no real reason for that. I assume it's because he is very close-minded about sex, but when I try to discuss it with him, he gets very angry and refuses to talk about it. I've been with my boyfriend for a year and my whole family approves of him. What do you think is the best way to talk to a dad to let me sleep at my boyfriend's house?" -Eve, age 19
"Eve, I'm going to disappoint you here. You say, 'There's no real reason he won't let you sleep there,' but he may have his own reasons, so give your father that much credit. I don't know your dad, I don't know what his reasons are, but one reason could be that he thinks sex and a relationship aren't the same thing. He may be someone who is traditional and wants you to be married or be older before he is comfortable with you having a physical relationship ...
You're 19 and legally an adult, why are you still living at home? If you don't feel like you're ready to be out on your own, maybe you're not ready to be. If you still feel like you need your parents' help, it might be an act of humility to say, 'If I need their help in terms of financial security, maybe it's not too much to ask to also accept their help in terms of relationship advice. I'm sure answer did not go over great with everyone."
3. "There's this boy, he is kind of mean to me and lies to me a lot, but then other times he's a really great guy. He says he likes me and he treats me really well, but how do you think I should perceive this relationship? - Charley, age 17
"Well, there's a little contradiction in here... if he lies to you and he's mean to you, he may like you but he's definitely not treating you very well. So, I would not waste my time with someone who lies to you. Even the 'mean to me' is easier to deal with than someone who lies to you a lot, because if he lies to you a lot, how do you know he even likes you?
I would give this person one last shot and say, 'Don't ever lie to me again, because I like you and you like me, but a predicate of that relationship is that we can't lie to each other.' And then kick him to the curb."
4. "I would really like to know all of the ways you can really tell if a person likes you - girls, boys, grown ups, everyone!" - Maria, age 19
"People show they like you in all kinds of different ways. But some basic ones are: They want to hear your stories, they care how you feel, they want to make your day better, they want to listen to your problems, they reach out to you. Everybody wants to be loved and have people pay attention to them, but if somebody goes through the effort to reach out to you, smile when they see you, ask you your problems, those are good signs that they like you because they're making the effort to not be so self-centered.
If your happiness is more important than their happiness, or if their more concerned with what's going on in your life than their life, that's a really good sign, because that's one nice definition of love."
Watch the full video and Colbert's complete responses below:
Now watch Tavi Gevinson, the 18-year-old founder of Rookie blog, on "The Colbert Report" last year: