Saturday, which aptly happens to be the day after Valentine’s Day, is the Love Hangover‘s fifteenth birthday. The concept is simple: a handful of duos, often assembled specifically for the evening, perform love-oriented songs. Friends Richard Alwyn and Caroline Mamoulides started the annual event in Raleigh in February 2000, and it has returned to Kings almost every year since (well, except for the years when there wasn’t a Kings). The concept has spread, with regional variations, to New York, Chicago, Kansas City and Ypsilanti. Mamoulides remains in Raleigh, where she organizes and plays in the Love Hangover show. We caught up with her and Alwyn to learn about the event’s past, present, and future.

INDY Week: What about each musician made you want them involved and paired the way they are?

Caroline Mamoulides: I asked Phil Cook to perform, and had some great partner ideas for him. Scheduling was not on our side, so he graciously suggested James Phillips. I was excited about this, loving the record James put out last year, and he suggested Christy Smith to join him, which was perfect, as she’s played the show before.

Oddly enough, a good friend and old band-mate of Christy’s, Staci Sawyer Phebus, and my old friend, Jer Warren, asked about doing the show back in November. They’ve just started collaborating, so this will be their musical debut together. This is another thing I love about the show, welcoming new blood to the mix and seeing them in a different light. For instance, most folks now know James Phillips as the drummer for Bombadil, so it’ll be a real treat to see and hear him as a lead in a duet. And you can really see that, looking at the lineups from past years: everyone growing musically.

And I recently reconnected with another old friend and past Hangover partner, Clay Merritt, while recording with the NC Music Love Army, and thought it’d be fun to get together again. I’ve always loved his voice and playing style, and it’s sentimental for me, being the fifteenth anniversary.

Seamus Kenney, of SNMNMNM, performed the Love Hangover in 2011, and he and girlfriend Kerri Lockwood have been working together on the Pop Up Chorus currently taking place at Motorco on Monday nights. This will be Kerri’s first Love Hangover and their musical debut together.

Brandy and Richard Flickinger are also known as The Revolutionary Sweethearts. Brandy will be coming out from behind the drums to play acoustic guitar for the show. She paired up with Erik Sugg in 2012 and we are excited to have her back. This will be Richard’s first Love Hangover. I had paired up one other duo who unfortunately had to drop out, but they’re on the list for next year, along with Phil Cook, so those details will have to be a surprise!

What was it like to have to find a new home while Kings was closed? In 2008, there wasn’t a Love Hangover. Was there a question of whether it would continue or not?

CM: The Pour House welcomed us with open arms in 2009. It was the tenth anniversary, a Sunday night and packed. There were folks sitting on the floor just in front of the stage. The tables were full and it was thick with bodies all the way back to the entry. They weren’t expecting such a crowd for our little show and had to call for extra barbacks. I think everyone really missed it in 2008, and a lot of service industry folks were finally able to make it on a Sunday so it was truly a special night. The reason it didn’t happen in 2008 was partly the downer that Kings was no longer, and that that winter was unusually busy for me. I absolutely missed the show, though, and was not going to let that happen again!

Can you explain how the Love Hangover expanded out of Raleigh and into other cities? Do you know of any places trying to get one started?

Richard Alwyn: In 2007, the third year Love Hangover was in New York, I asked Dana Kletter to play with my friend Scott Easterday from Kansas City, where I grew up. They had never met, and I think they may have rehearsed a couple of times by phone. But they’re both musical geniuses, so after an hour or so of rehearsal in person at my apartment, they played the show and sounded brilliant. Following that, they both took the show to new cities. Scott started The Love Hangover in Kansas City, Mo., in 2008, and has hosted it there ever since. By 2009, Dana had relocated from Boston to Ann Arbor and started a show there with 826 Michigan, who continue to host it in Ann Arbor and Ypsilanti.

Also in 2008, Erin McGrane put on a Love Hangover show on the 28th of February. In 2009, she came to NYC and played the show with Jeff Freling, a Kansas City transplant living in Chicago and playing in the Blue Man Group, and she also emceed the NYC show. Erin and Jeff started the Chicago chapter in 2010. This year there is no show in Chicago, but Erin and Jeff are playing the Kansas City show as “antique pop” duo Victor & Penny.

It looks like each town does it a little differently. Is that the case?

RA: Every city does it a little differently and I would hope every duo does it a little differently. To me, the only rule that must stand is that the songs have to be about love. The artists are encouraged to interpret that theme any way they choose. The duet setup ensures there are at least two sides to any story. And on occasion, different duos have been augmented with a guest or two. In 2003, when Caitlin Cary and I played “Fairytale of New York,” we had Jen Gunderman join us on accordion.

What are some standout performances? And didn’t The Small Ponds form at a Love Hangover?

CM: There are too many standout performances to list! It is such a special show, in that two folks who typically don’t perform together collaborate on songs we all know and love, songs we grew up with and new favorites. Sometimes I pair folks, sometimes I’ll ask one person to ask whomever they like, and sometimes folks approach me with an idea. A friend mentioned thinking it’d be fun to see Phil Cook and Sara Bell do the dueling banjo thing, so we made that happen in 2010.

Other highlights are Lynn Blakey and Chip Robinson performing “Send In The Clowns” in 2002, Aimée Argote and Daniel Hart taking on “Whole Lotta Love” in 2006, Katrina Lamberto and Joey Fralin performing “Lady” also in 2006, Ashley Carter and Jeff Crawford covering “Rid of Me” in 2011, and Brandy Flickinger and Erik Sugg’s beautiful version of “I Wish I Never Saw The Sunshine” by the Ronettes in 2012. And, yes, The Small Ponds formed after Caitlin Cary and Matt Douglas’ collaboration in 2009. Their entire set was magical.

My personal favorites are “Every Time We Say Goodbye” with Scott Phillips at the very first show in 2000, “You & Your Sister” with Clay Merritt in 2005, and “Don’t Throw It All Away” with Kenny Roby in 2012.

With this being the fifteenth anniversary, can you tell me what the future holds? How long do you plan on organizing these?

CM: We’ll keep going! And I imagine at some point I’ll pass the torch. I try to mix it up each year with veterans and rookies alike, and so far everyone gets hooked, so I know it’ll one day go into excellent hands.