1. Sam Holt

Is it better to date a gamer girl, and is it worth waiting/holding out for one, or is that more trouble than it’s worth?

2. Ryan Lowey (“Lowey”)

I’ve had a crush on a girl all four years of high school, she’s finally single, and graduation is days away — do I confess my feelings now or let it go?

3. Brian Evans

I’m 17 and like a 19-year-old college guy who drinks and has a bigger sexual history, and I’m straight-edge and jealous — should I pursue this or move on?

4. Jason (PlayStation Home romance)

Not really a question — he’s sharing a success story: met a girl in PlayStation Home, visited her, they fell in love, got married, and are now happily “knockin boots.”

5. “Phil A. Nursehole” (fake name)

I was set up with my friend’s younger, wild sister, we’ve been hooking up, and I just found out she’s married and her sister hid it — do I break it off, keep enjoying it, or shoot for a threesome with both sisters?

6. Jimmy Wills

I’m 17, like a gamer girl on the opposite side of the county, and I can’t drive yet so my parents would have to drive and wait during dates — should I still ask her out/start a relationship

7. Unnamed female listener (pet names)

I’ve lived with my boyfriend for almost 3 years, we’re solid, but we never use pet names (no “baby,” “honey,” etc.) — is that weird or a bad sign?

8. Steve / Stephen Pritchett

I’m 24, never dated and never had sex, and I’m scared of relationships even though I want one — is it wrong that I’m still a virgin, and how do I get past this fear?

8. Anthony (Kendra vs Kim Kardashian sex tapes)

The Kendra sex tape is reportedly more popular than Kim Kardashian’s — how is that possible when Kim seems hotter?

9. Gabriel Blaine

I’m 19, look very young/baby-faced, don’t go out much, and feel girls my age want older-looking guys — how can I start actually meeting girls and not be stuck “never knockin boots”?

10. Brad in Nashville

Not really a question — he writes in to share advice/ideas on where to meet women after college (Junior Chamber of Commerce, Bible study, etc.), and mentions he married a drinking buddy’s little sister.

11. Jordan Williams – “Big black guy needs love”

I’m 6’9”, upper-300 lbs., known as the big, funny “big black guy” / teddy bear, but that persona keeps getting me friend-zoned — should I change myself/lose weight to get dates, or just keep looking for the right girl?

12. Sean Malley

I’m 16, homeschooled in a small town, never had a girlfriend or kissed a girl. Daemon once said by 14 boys should have at least kissed someone — am I behind/abnormal because I haven’t?

13. Andrew

I’m 23 and went on a date with an 18-year-old co-worker; we had a romantic night and kissed — is the 23/18 age gap okay, or is that a problem?

14. Isabel (female listener, fiancé in BASIC)

My fiancé is coming home from basic training after 3+ months away, and we’ll be having lots of sex — what can I do in the bedroom to really surprise him and make it extra special, not just our usual “kinky” stuff?

15. Tyler Robinson

I’m 17, have been with the same girlfriend for 2 years; she’s a strong Christian who believes in no sex before marriage, but I really want sex — what should I do: stay, push boundaries, or move on?

16. Pierre from the Pacific Northwest

I’m 24 and intentionally saving sex for someone I truly love. I’ve done everything up to “third base” (oral, heavy fooling around) — am I still a virgin?

17. Michael Lin

He’s responding to an older listener question about dating your brother’s ex. He doesn’t really ask; he shares a cautionary story: his wife’s mom dated a guy, then married that guy’s brother, and it makes family gatherings super awkward — basically saying “please don’t do this; it messes up your kids’ lives later.”