You Asked It

Ask a Grown Man: Stephen Colbert

“A really good sign somebody likes you is if they bring you cookies.”

Once upon a time, Stephen Colbert, the lovely and hilarious host of our favorite political talk show, The Colbert Report, graciously invited our bosstone to be on his show. During their interview, he asked Tavi if we might maybe think about considering having him do an Ask a Grown sometime. Our answer, of course, was, “Hell yes, you wonderful man!!”

Now, we’ve cashed in on that generous offer to bring you this video containing SC’s wise advice about misogynist jokes, boyfriend-based dilemmas, and how to tell if someone thinks you’re cool. And, Stephen, we’ll make that last one easy for you: WE THINK YOU’RE *EXTRAORDINARILY* COOL.

If you do too, you can follow Sir Colbert on Twitter, catch the Report on Comedy Central on Monday through Thursday nights every week, and/or just watch this here video and be like, “Hell yes, you wonderful man!!”

Is your life just way too confusing to even deal with right now? Why not ask a non-terrible adult about it? Email questions to with “Ask a Grown” in the subject line, and please include your first name (or nickname or initials), city, and age.


  • Abbey xoxo July 30th, 2014 12:01 AM

    I was so glad to find that Colbert was doing Ask a Grown Man! This made my evening, and the last question really hit home with me. I’ve been through kind of a confusing time with trying to determine if someone I know and like a lot likes me, too. :)

    P.S. The Spanish word for cookies is “galletas”

  • Claire July 30th, 2014 12:19 AM

    Probably my favorite Ask a Grown Man to date. Also, his flannel game is seriously strong.

    Now for Jon Stewart…?

  • LittleMoon July 30th, 2014 12:36 AM

    He’s got great answers. <3<3<3

  • emseely July 30th, 2014 2:31 AM

    STOP NO THIS IS TOO PERFECT stephen colbert is the Cool Dad of my dreams

  • Elizabete July 30th, 2014 4:56 AM

    Aww, this was super cute and S. Colbert seems like a sweet person. I just really liked those answers and while they weren’t anything new a pair of them were pretty relevant to my current interests, haha.

  • Lorelei July 30th, 2014 11:53 AM

    He seems so nice! And when he said “however you say cookies in Spanish” out loud I said “galletas”

    (Ask A Grown Woman suggestion: Sarah Silverman)

  • Maradoll Mynx July 30th, 2014 1:13 PM

    I really didn’t think it was possible for me to LOVE Stephen Colbert an ounce more. But now I do :)

  • RosieLML July 30th, 2014 1:25 PM

    Gosh it’s so weird seeing him like out of character! Also I feel the need to point out that Stephen Colbert is my fav person ever. EVER.

  • buzzy July 30th, 2014 1:31 PM

    Awesome. Grown Man Request: Pete Holmes please!

  • lydiamerida July 30th, 2014 7:21 PM

    omg….. he would be like the best supportive uncle in the world

  • Abby July 30th, 2014 9:35 PM

    So I love this all, but I wanted to throw out there how important I think it is how he recognized that he said something that might be offensive to Native Americans. I thought that was amazing… because obviously it would be better if no one said offensive things, but I think they slip out sometimes, and it’s sooo amazing when people can own up to them and apologize instead of trying to explain it away. We can’t be perfect, but owning up to our mistakes gets us a little closer to perfect.

    PS this was AMAZING and I screamed a little when I saw it.

  • honorarygilmoregal July 31st, 2014 12:12 AM

    This is great! I love Stephen Colbert and the Report.

  • janevtiamat July 31st, 2014 6:17 PM

    Stephen Colbert is great! He is so inclusive in his answers.

  • AidaA July 31st, 2014 8:43 PM

    Stephen Colbert is literally the reason I’m selling my shoes to do a writing course at Second City. I have so much love for him!! Third for Jon Stewart and maybe I’m saying this because I’m still excited that I met him in London tonight: Conan O’Brien!!

  • dancinggrapes August 1st, 2014 3:16 PM

    This is so lovely and the idea where people can be earnest in their questions and answers is wonderful. I do want everyone to know that while sometimes boys may be mean because they are afraid you don’t like them (like Stephen says), you deserve to be treated nicely. Please let people know that their behavior is hurting you and if they don’t change let them go because your life should be full of great people and things.

  • Shonagon August 2nd, 2014 10:19 PM

    His daughter is one very, very lucky girl. Imagine growing up with a dad this cool who is also loving and understanding. His answers were clearly from his heart, he seemed to make a real connection with each girl to whom he spoke.

    He’s the best! I’ll miss the Colbert Report but I’ll watch him anywhere and anytime.

  • anniebkidgenuis August 3rd, 2014 1:55 AM

    i have the biggest dad crush on stephen colbert (as in he’s a dad but i still have a crush on him) and this video melts my whole entire heart and rookie i love you for doing this

    (jon stewart is my other major dad crush and i would fully support an ask a grown man j-stew edition)

  • dessertstealer August 5th, 2014 3:09 PM


    Please get Jon stewart for the next Ask a grown man !!! I love him!!!