Imogen Valentine Talks “Same Font Different Man,” Growing Up, and the Next Chapter of Little Miss Optimist

There are some realizations that only seem to happen when you’re comparing notes with your friends.

For Imogen Valentine, “Same Font Different Man” started exactly there: walking home from a wine night, talking through relationships and breakups, and realizing that even when the people involved were completely different, certain patterns had a habit of repeating themselves.

“I was walking home from a wine night with a few girlfriends, and even though every relationship and breakup is different, we realized there were so many commonalities and recurring patterns in our stories,” Imogen tells Everyday Jams. “The phrase just popped into my head, and I thought it was kind of funny, but it also encapsulated the whole conversation.”

It was the kind of phrase that was too good to leave behind.

Imogen keeps a running Notes app filled with song titles and concepts, often beginning with an idea before working her way toward the song itself. “Same Font Different Man” immediately made the list.

“I put it at the top of the list and knew I wanted to come back to it,” she says.

Same Font, Familiar Patterns

She eventually brought the idea to one of her closest friends, songwriter Isabella, knowing there was something worth chasing.

“I sent it to one of my best friends, Isabella, before the session because I knew she’d be the perfect songwriter to build the idea out with,” Imogen explains. “I was pretty set on the concept and just had a feeling there was something there.”

Together with producer Chedda, they turned that one-line observation into a song that finds its strength in not taking itself too seriously.

The stories underneath it are real, but “Same Font Different Man” never feels interested in becoming a takedown. Instead, Imogen leans into the absurdity of recognizing the same behaviors in different people and finding a way to laugh at something that probably wasn’t very funny while it was happening.

The trust between Imogen and Isabella helped make that possible.

“She knew all the ins and outs of that relationship, and I think the saying is true: men come and go, but the inside jokes about them with your girlfriends are forever,” she says.

That familiarity gave Imogen room to write without guarding herself first.

“I don’t think I would’ve been as unfiltered with someone who didn’t know me or my personal life that well,” she says. “Having that trust meant I could say everything I needed to, and then we could refine it and find the humor together.”

Finding the Fun in Hyperpop

It is a sharp song, but it is also a fun one, and sonically, Imogen wanted the production to reflect that.

While her music often lives somewhere between dream pop, intimate songwriting, and nostalgia, “Same Font Different Man” pushes further into a more electronic space. Imogen sees some connection to “Encrypted,” a track from Little Miss Optimist, but considers the new single its own moment rather than a direct continuation of the EP.

“To me, this song feels like a bit of an extension and evolution of ‘Encrypted’ sonically, but it also sits a little more separately from the rest of the EP,” she explains.

That separation is intentional. “Same Font Different Man” will remain a standalone single rather than appearing on the upcoming deluxe edition of Little Miss Optimist.

“I wanted to lean more into a fun, electronic sound for this one because, like ‘Encrypted,’ I feel like ‘Same Font Different Man’ is meant to be tongue in cheek,” Imogen says.

It also gave her the chance to try something she had not really explored before.

“I had never really dabbled in the hyperpop world before, but I’d been listening to a lot of Tiffany Day and Underscores this past spring and wanted to explore that sound a little and figure out how to make it feel like me.”

Building the Visual World

That same mix of old and new carries into the song’s visual world.

The music video places Imogen at a typewriter, turning everything she has been thinking into her own written manifesto. The imagery feels nostalgic by design, even as the production underneath it moves into more modern territory.

“I love having a nostalgic tinge to my visuals, and I really liked the idea of juxtaposing that with the hyperpop, modern production,” she says.

The typewriter became a playful way of literalizing the song’s premise while reclaiming another familiar idea in the process.

“It felt like a lighthearted way to take that whole ‘woman scorned’ idea that I think tends to be pushed onto women and reclaim it for myself.”

For Imogen, music and visuals have never really existed separately anyway.

She jokes that while she wishes she had synesthesia, she experiences something closer to a visual version of it. Songs tend to arrive with imagery attached.

“I’m always picturing the world around a song and imagining what the music video could look like,” she says.

With “Lady Karma,” for example, she could already see herself in angel wings walking through the city long before the visual was fully realized.

“I would see that image every time I closed my eyes and listened to the song.”

Between London and New York

That instinct has helped shape a world around Imogen’s music that feels soft and nostalgic without being stuck in the past.

Born in London and now based in New York, Imogen points to both cities as important parts of the artist she has become.

“There are so many legendary artists who have come out of the UK, and the music culture is so rich and diverse,” she says. “I also love British humor, so I think all of that became part of my foundation and reference points.”

New York, meanwhile, became the place where she says she grew more fully into herself.

“I really grew into myself in New York, which also has such a rich music history and in my experience an incredible emerging artist scene,” Imogen says. “Over the past few years, I’ve been able to immerse myself in that community and be exposed to so much music and talent.”

“I think that combination shows up in the way I write and in the worlds I build around my music.”

Writing With More Perspective

That evolution becomes especially clear when Imogen looks back at her 2024 debut EP, Ouch!

“I swear a lot less!” she jokes.

But underneath the joke is a real shift.

“With Ouch! I was feeling a little more emo and rebellious and was like, ‘Oh, I can say that! Why not?’ Whereas now I feel a lot more intentional about the stories I want to tell and how I want to tell them.”

During that period, Imogen says she felt “a bit like an open wound,” something that naturally found its way into the writing. Now, the honesty is still there, but she approaches it from a more grounded place.

“I definitely don’t censor myself, but there’s a little more grounding and discernment in how I write,” she says. “That’s not to say I don’t still love some colorful wording, though!”

Returning to Little Miss Optimist

That growing perspective is also at the heart of the forthcoming deluxe edition of Little Miss Optimist.

Rather than closing the door on the project after its original release, Imogen realized she still had more to say inside of it.

“After I filmed the ‘Lady Karma’ music video in February, I just loved the world of the project so much and felt like there was still a lot more to excavate, both visually and in my songwriting,” she says.

As she continued writing, the newer songs began moving beyond the girlhood explored in the original project and further into the realities of womanhood.

“A lot of the songs I’ve written over the past nine months have delved further into different aspects of girlhood and womanhood, so it felt like it made the most sense for them to live within the world of Little Miss Optimist, rather than moving on to a new project.”

For Imogen, the deluxe also captures the perspective that comes from simply having lived a little more.

“I wrote Little Miss Optimist between 2022 and 2023, when I felt more on the cusp of womanhood,” she explains. “I think the songs on the deluxe feel a little less rooted in girlhood and more in womanhood, and in navigating both the internal and external experience of being a woman in your 20s and trying to figure it all out, but with a little more perspective and life lived.”

Hearing the Songs Differently

Imogen has also found new ways into the world of Little Miss Optimist by revisiting its songs acoustically.

Stripping back the production gave her a chance to hear the writing itself with a little more clarity.

“When you take away a lot of the production, there’s nowhere to hide, and I think I heard the lyrics and emotions a little more clearly,” she says.

It also tapped into one of her longer-term goals.

“I’ve always loved NPR’s Tiny Desk, and doing one is definitely a goal of mine as an artist, so this felt like a fun little mini version of that for me and maybe a bit of a manifestation for the future.”

Growing Up Without Losing the Fun

For all of the sonic shifts, visual ideas, and new perspective surrounding Imogen’s work right now, there is a simple thread running through it all: she is letting herself change without abandoning the world she has already built.

“I feel like I’m growing up a little,” she says. “I’m excited for listeners, whether they’ve been listening for a while or are just discovering my music, to grow up with me.”

“I hope they can see themselves, or little pieces of themselves, in the experiences I’m writing about and feel like they’re coming along for the ride.”

For an artist whose songs make room for vulnerability, humor, softness, and reinvention, “Same Font Different Man” feels like another piece of that process, proof that growing up does not necessarily mean becoming more serious.

Sometimes it just means getting better at recognizing the pattern.

And knowing exactly what font it’s written in.

Stream. “Same Font Different Man” now, and keep up with Imogen Valentine as she steps into the next chapter of Little Miss Optimist.