Hot Love: How to Ask Out the Barista While Listening to Squeeze

Dave Hill helps the lovelorn get it on and get over it.

Hot Love is a new 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 just got a job in a new city and I’m so excited! The problem is, my boyfriend doesn’t want to move with me at least right now. He says he’s looking, but I’m so worried. Does long distance ever work?

Long Distance Operator

Dear Long Distance Operator,

First of all, congrats on your new job in that new city. Also, be sure to try the shrimp cocktail there. They do it the best in my opinion, and trust me — I know from shrimp cocktail.

Now for your question. I say give the long-distance relationship a go and, eventually, if there is enough love, lack of options and/or co-dependence happening, you two will wind up living in the same city together again — hopefully the one with the shrimp cocktail. Also, if you do wind up together, I hope it’s for love and not either of those other two reasons. You are the best and I just want you to be happy.

Anyway, with the long-distance scenario there is, of course, the chance that it won’t work out — you might meet somebody new in your fun new city, your boyfriend might accidentally get his dick caught in something or who knows what else, really. But, hey, at least you tried and won’t ever have to wonder “What if?” and end up stalking each other on Facebook until we all die in the inevitable global fire.

I’m realizing I didn’t answer your question about whether long-distance relationships ever work. The answer is yes, sometimes, but usually not for long. Still, the fact that you’re even asking suggests to me that you’ve got enough sass and moxie to hold up your end of the deal. I just hope your boyfriend gets his act together. I am so tired of his bullshit.

My song for you is “Out There” by Dinosaur Jr. You can hum it to yourself while you’re grocery shopping or whatever all alone in your fun new town. Also, there is a sweet guitar solo, which is great for everybody.

Happy to help,

Dear Dave,

I am in love with my barista. She flirts with me ALL the time. How do I ask her out? If she says no, do I have to find a new coffee shop? So many questions.

Thanking you in advance,
Flat White

Dear Flat White,

First of all, calm down, she’s not flirting with you “ALL” the time. Some of the time, maybe, but let’s not act like she doesn’t have a job to do. Anyway, with that out of the way, let me just say that I have fallen for many a barista in my day. One of them was even missing an arm, but I stared into her eyes so intently each day, it took me months to even notice. Also, she had a prosthetic limb, so I never thought twice about it, really — even when she would spill hot drinks on it and not even flinch. I know you think I’m making up this whole one-armed barista thing up, but it’s true.

Now back to your question. You must act fast in this scenario because most dream girls (and for the sake of optimism, I will assume your barista, in fact, is) don’t hold onto barista jobs for long. It tends to be a job people have while they’re waiting for, or actually trying to make, something else happen. One day she will probably be long gone, so you mustn’t dally. Just do it. If she’s interested, she’ll say yes and, assuming it goes well, I’ll bet my espresso machine* she’ll start slipping you the occasional free or at least discounted coffee in no time — one of the perks (pun intended) of dating a barista. And if she says no, it’s up to you whether you need to find a new coffee shop. Odds are there are already several customers who walk in there every day whom she finds way creepier than you, so I wouldn’t sweat it.

One last thing, since she works at a coffee shop, asking her out for coffee probably isn’t an option. Literally any other beverage will do the trick. Then again, maybe the whole reason she works there is that she loves coffee. Oh, man, now I’m getting nervous and confused. Anyway, let me know what happens.

My song for you is “Black Coffee in Bed” by Squeeze. A little on the nose maybe, but Squeeze is pretty underrated if you ask me and that song is a total jam. Then again, the song is about a dude who just lost his woman. Oh, man. I’m sorry about that. Life isn’t fair but you seem great so I wouldn’t worry about it just yet.

Happy to help,

*I don’t really have an espresso machine. I am a man of the people.

Dear Dave,
How can you tell if someone is cheating on you?


Dear Worried,

There is only one way to find out: you must smell the genitals. All other information is inconclusive.

My song for you is “Me and Mrs. Jones” by Billy Paul. It’s about a dude who has an affair with a married woman. As best I can tell, they mostly have lunch together, but I bet they get up to plenty of boning too.

Keep me posted,


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.