Hot Love: How to Finally Make Out with That Shy Guy While Listening to Prince

Dave Hill dishes out love advice — and love songs — to the lovelorn.

Hot Love is a column by comedian, writer and musician Dave Hill wherein he helps the lovelorn with advice on love, relationships and porking. Please send your questions to [email protected].

Dear Dave,

I’ve gone on like six dates with this guy and he has yet to kiss me. Am I doing something wrong? Am I supposed to make the first move? Help me, Dave!

Thank you so much,

Dear Waiting,

Oh, man, I have sooo been there. And I am certain if we opened this question up to the literally thousands upon thousands of people who read this column every single time it appears here on this website, we would get all sorts of different answers and opinions on this topic. But since I’m the one getting paid the big bucks here, I’ll just tell you what I, Dave Hill, love expert, think.

There was a time, of course, when the guy would be expected to make the first move no matter what. And if he didn’t make a move, well that was the end of that. Ask around. But these are modern times, dammit. I mean look at us: we’re on the Internet and one of us is wearing shiny pants (HINT: me)! How cool is that? Anyway, my point is, if I were you and still interested in this guy who, as long as we’re on the topic, is either very awkward and shy or simply not interested in being more than friends as best I can tell, next time I was on a date with him, at some point I’d just look at him all sexy like and say something along the lines of, “Hey, buddy, you wanna make out or not? My programs are on!”

If he does want to make out, he’ll probably just be all like, “Yeah!” and then totally start making out with you. And if he doesn’t, you can just ask him to pull the van over, get out, and get on with your life, dammit. That said, it sounds like you like this guy, so let’s hope he’ll be into the making out thing mentioned earlier and then you won’t have to get out of some weird van on the side of the road. Believe me, I’ve been there, and even when you’re in some strange town where nothing, not even your own face in the mirror, looks even the least bit familiar, it can really mess with your head. I guess I just want you to know I’ve got my fingers crossed. For both of us.

My song for you is “Kiss” by Prince. A little nose maybe, but come on — now there’s a guy who knew a thing or two about making out.

Just doing my part,

Dear Dave,

None of the girls I like pay any attention to me, and I’m not interested in any of the girls who seem to like me! I’ve had a few friends tell me that my problem is going for girls who are out of my league, but I don’t know what else to do! Help?

Tired of Being Alone

Dear Tired,

You need to listen to the Buddha. I just talked to him and he said you need to free yourself of desire, specifically the desire to meet ladies. Read a reasonably good book, learn how to do that thing where you jab a knife really fast in between all your fingers on an old wooden table to the delight and amazement of everyone else in the spy bunker, at least one of whom will ideally be wearing an eye patch, or maybe learn more about exotic birds or some shit. But don’t even think about meeting girls, not even for a minute. And once you have truly mastered not thinking about girls (and that thing with the knife, the more I think about it), that’s when some smoking hot chick is gonna walk up to you and be all like, “Hey, you wanna go to Cinnabon with me or something?” At least that’s how it happened with me, anyway. I guess what I’m trying to say is, calm down. She’s out there. I just know it. Also, seriously, how cool would it be to get good at that knife thing? Dangerous, sure, but totally worth it.

My song for you is “Out There” by Dinosaur Jr. There’s a pretty sweet guitar solo in that song, too, which is actually cooler than the knife thing I won’t shut up about.

Glad I could help,

Dear Dave,

I just broke up with a girl who moved into the apartment next to mine while we were dating. Now I still see her all the time, and she spends a lot of time with my roommates, but I’m looking to move on and meet new people. How can I do that without things getting super awkward?

Boy Next Door

Dear Boy,

I don’t normally like to use the word “bro,” but seriously, bro, what the hell were you thinking having a girl you were dating move in next door, bro? You were pretty much begging for this exact scenario to happen, bro. And now you have two choices: either move and avoid the whole situation altogether or just be all like “F it” and get on with your life while being respectful yet not overly concerned about how your ex feels about you moving on and meeting someone new, bro. Then again, if you do stay, bro, I suppose you could talk to her about all this and let her know that you’d like to be respectful of her and her feelings but you’d also like to move on and meet some new people. I have a feeling that conversation is going to go great. Also, when you do meet someone new, don’t have them move into the same building, bro. Haven’t you learned anything, dammit?!

My song for you is “Where Eagles Dare” by the Misfits. I’m honestly not sure if it’s really relevant here, but dammit if it isn’t a stone cold jam and a half.

Your bro,

Dave Hill is a comedian, writer, musician, and highly boneable public figure. He is the author of the book Tasteful Nudes (St. Martin’s Press, 2012), host of The Goddamn Dave Hill Show on New Jersey’s WFMU-91.1, frequent contributor to This American Life and singer-guitar player for the power-pop band Valley Lodge. His new comedy album Let Me Turn You On is available now, as is his second collection of essays, Dave Hill Doesn’t Live Here Anymore (Penguin/Blue Rider Press). Dave also smells incredible and can play sweet guitar solos without even really trying. You can follow him on Twitter here.