Madeline May went into the first date with low expectations. She was tired of dating apps. She wasn’t expecting anything special.
Unexpectedly, the laughter, chemistry and conversation flowed. But just as quickly as Madeline’s hopes for a second date were raised, they were dashed. Her date, Boyan Vassilev, revealed he was departing on a three-month trip to Bulgaria the next day.
“It’s unfortunate,” he told her. Madeline agreed, but quickly shrugged off the disappointment.
“We had a great first date. I enjoyed him. We would have gone on a second date had the circumstances been different,” Madeline tells CNN Travel today. “But it was just two ships passing in the night, and it didn’t work out. Wrong timing, and that’s fine. That’s all it was.”
Boyan was born in Bulgaria, but his family moved to Arizona when he was a kid. The family often returned to the Eastern European country for vacations, and Boyan ended up staying there for a chunk of 2024.
Meanwhile, within six months of her first date with Boyan, Madeline met and started seriously dating someone else. She kept up, loosely, with Boyan on social media — enjoying the occasional snapshots of his life in the US and Bulgaria. But her focus was on her relationship and her busy career.
Cut to mid-2026. 31-year-old Madeline was feeling increasingly dissatisfied with life. She wanted to see the world and felt she’d only seen the midwest, where she was from, and Arizona, where she was living at the time.
“Always gnawing in my mind was the thought that I need to find time to travel,” says Madeline. “And I knew that to travel in the way I wanted to, I was going to need to quit my job.”
And so began what Madeline calls her “corporate crash-out.” She left her comfortable job, broke up with her boyfriend and booked a one-way ticket to Europe.
“I started in Switzerland, built my plans from there … and I ultimately decided to go to Bulgaria.”
Madeline wasn’t — in case you were assuming this is a love story — going to Bulgaria for Boyan. She just figured Sofia, the country’s capital, would be a fun, different place to visit and a great second stop on her European adventure.
But recalling her long-ago date’s Bulgarian link, she decided she had nothing to lose by messaging Boyan on social media, asking if he had any recommends or tips.
It did occur to her that they were basically strangers. They’d originally met on a dating app. He was “just this guy that I went on one date with one time,” says Madeline, laughing.
But Boyan sent her a friendly reply, listing recommendations in Sofia. He offered to put Madeline in touch with friends and, because his parents always spend their summers in Bulgaria, said he could link her up with his mother.
Madeline remembered Boyan talking about his mom, Maria, on their date. She sounded, thought Madeline, like an interesting person. Maria had an impressive academic career in the field of electrical engineering — the family had moved to the US when she got a research job at the University of Cincinnati. She later worked at Arizona State University and recently retired from Boise State University.
Madeline thought she’d love to be shown around Sofia by Maria.
“So, I was like, ‘I’d meet your mom,’” she recalls. “Basically, I’m calling your bluff, dude. If you’re offering your mom, I will do it … I don’t know what compelled him to introduce me to his mom.”
But Boyan wasn’t bluffing. He passed on the phone number for his mother, Maria Mitkova.
“He goes, ‘She doesn’t text much, so give her a call.’ I was like, ‘Can you just give her a heads up that some girl you know from the United States is calling her?’”
Boyan reassured Madeline that Maria would be expecting to hear from her. And so, when Madeline got to her accommodation in Sofia, she hit dial.
“And this just ended up being one of the best things to ever happen in my life,” Madeline says today. “And it started so casually.”
Madeline felt apprehensive as the phone rang, but as soon as Maria picked up, her uncertainty melted away.
Maria was warm, welcoming, kind and enthusiastic.
“She was talking my ear off on this call, saying all these plans she wanted to do,” says Madeline.
Maria suggested a traditional Bulgarian breakfast at her home the next day, followed by a tour around Sofia.
“I’m like, ‘You don’t even know me, girl. I am a stranger to you, and here you are making all of these plans with me,’” recalls Madeline. “I was so immediately grateful.”
“My son told me that he gave her my telephone number,” Maria tells CNN Travel today. “I was wondering if she will call me or not, because not all young people are happy to talk to much older people — but she called me.”
As a professor, Maria has always enjoyed interacting with her young students, engaging with their curiosity and learning from them in turn. She was more than happy to propose breakfast followed by a day of sightseeing.
“And so, I think it was very natural to have a nice chat with her,” says Maria. “We found out that we have similar interests. She plays piano. I play piano. I have a piano in all my houses in America, in Bulgaria, everywhere. We talked about this, and she travels, also, a lot.”
The next morning, her first in Sofia, Madeline headed to Maria’s home. En route, she bought a potted flower as a thank you gift.
Maria opened the door and immediately greeted Madeline with a “big smile and a hug.”
“She’s so friendly; she’s so open,” Madeline recalls thinking. Her next thought was: “Wow this woman is gorgeous. She’s got perfect eyebrows.”
Immediately, Madeline and Maria started talking. And didn’t stop.
“She’s a wonderful young person,” says Maria of Madeline. “Beautiful, smart, open-hearted. We didn’t have any problems starting the conversation. She gave me a very nice flower, which thrilled me because I didn’t expect this, and it was very nice of her to think how to enter my home, how to present herself.”
Maria’s husband was recovering from a hip injury, so he joined the welcome breakfast, then left the women to their walking tour adventure, with Maria leading the way.
“She puts on her hot pink tennis shoes,” recalls Madeline. “And just bounces down the stairs — all the way down these six flights of stairs — for us to go walk around the city.”
Maria focused on Sofia’s center: the parliament, the university, the library. She also took Madeline to a restaurant that hadn’t changed much since before the collapse of communist rule in Bulgaria in the late 1980s.
“For the foreigners, it’s very interesting because it is full with some furniture, some other stuff from the socialist time, so that they could get an idea of our environment at that time,” says Maria.
She talked to Madeline about how her family had owned their apartment for decades — it’s now renovated to 2026 tastes, but once it had resembled something closer to the restaurant decor.
A lot of their conversation that first day revolved around Maria’s experiences living through the communist era. Madeline was fascinated to hear about Maria’s experience as a younger woman.
“It’s so fascinating that she grew up in socialism,” says Madeline. “The tough times that she had, how she would sneak clothes over the border for her family when she would travel for research, and just incredible stories. Her grit is absolutely inspiring.”
“She didn’t know a lot about how life was at that time and how the different countries interacted and how they were living under Russian hegemony because we were not an independent country,” says Maria.
It was also amazing, says Madeline, to see Sofia through a local’s eyes. She took her to the city’s open-air Women’s Market, which dates back to the 19th century, to buy her favorite spices, which she mixes with beans while making soup.
“Maria knew what to do there,” says Madeline. “I think if I had showed up at the Women’s Market, I would have not known what to do, not known where to go.”
But Maria led Madeline to her favorite stall.
“I felt less like a tourist in Sofia, and so much more like a local,” says Madeline. “Sofia is a top three city for me, and of course I’m recommending it — I have to recognize my bias that Maria was a huge part of why my time was so special there. Had I not had Maria, I do think I still would have really, really enjoyed Sofia. But obviously, she’s what made the city for me.”
“Turns out she was way more fascinating and a way bigger part of my time there than anything else.”
As the two bonded over music and the piano, Maria invited Madeline to a performance by Khatia Buniatishvili, a Georgian-born pianist, on the opening night of Sofia Philharmonic’s season at the Bulgaria Concert Hall.
“One of the best female pianists in the world, what an opportunity,” says Madeline.
The only issue? She had nothing appropriate to wear.
“I packed so light for the whole trip,” says Madeline. “I asked her, ‘What are you going to wear?’ And she’s like ‘My little heels and a gold shawl.’”
Madeline went thrifting. She found a gorgeous black jumpsuit and sandals for $10.
“That was part of the fun, too,” she says.
Before the concert, Maria and Madeline went to dinner with two of Maria’s close friends.
“I’m sitting there with the three ‘Golden Girls’ of Bulgaria, basically just a really fun group of older women from Bulgaria,” says Madeline.
When she opened up to the women about her recent breakup, the three women proved themselves to be great listeners and Madeline left feeling buoyed and supported.
“It was a really big deal for me,” says Madeline. “Very healing.”
Madeline says she appreciated the “cross-generational friendship” aspect of her relationship with Maria, which involved Maria offering advice and wisdom, but never talking down to her.
“I never got the vibe that she felt like my mom or my grandmother. She is her own person, who is just an older woman in my life now that I’ve connected with,” Madeline says. “An inspirational woman who I would love to be like, I want to be.”
Maria, who interacts on a daily basis with students, says she’s never treated her connections with younger people as any different than her friendships with her peers.
“I know that they are normal people who have a little bit less experience than me, but that’s my role to give them my experience so that I can help them grow,” Maria says.
She felt a kinship to Madeline, and found lots to admire in her outlook on the world.
“I liked very much that she is open-hearted. She looks at the world with open eyes, willing to understand the truth about everything that she is seeing,” says Maria.
Madeline was originally planning to stay in Sofia for only three days. She ended up in Sofia for two weeks. On their final meet-up, Maria gifted Madeline a necklace, which, other than when she went rafting in Slovenia, she’s not taken off since.
“It’s on me right now,” says Madeline. “Have not gone a day without it.”
Since Madeline moved onto the next stop on her European adventure, she’s chatted on the phone with Maria “many times.”
She mailed Maria postcards from North Macedonia — where Maria’s mother was born — and continues to update her on her travels. She’s currently enjoying Krakow, Poland and is about to head to Bratislava, Slovenia.
“In a motherly sense, she does message me and says, ‘I hope you’re doing okay, I hope you’re safe. I’ve been thinking about you,” says Madeline of Maria.
Maria says she hopes the two friends will see each other again before long, either back in the US or Europe.
“I have many stories to tell her,” she says.
In the meantime, Maria is very encouraging of Madeline’s travels. Madeline says Maria’s encouragement helped her feel validated in her choice to take a risk and leave her stability in the US.
“She has full faith in me, and that’s just that’s so special,” says Madeline.
For Madeline, the friendship story is proof that risk-taking can pay off.
“I guess it was weird that I reached out to a guy I went on one date with, and he set me up with his mom. But if I hadn’t done that, this whole situation wouldn’t have happened,” she says. “You just have to open yourself up and say yes to things, and hope for the best … Human connection is so important.”
Madeline recently shared the story of her friendship with Maria on Instagram, where she’s been chronicling her travels.
“There are people on my comments going, ‘How do I find my Maria?’ And other women are commenting: ‘Join your local knitting club. Go to the nursing home. Go to whatever other thing is going on in town.’ These people are out there. These connections are out there. But you do have to seek them out. They’re not going to show up at your doorstep. Make human connections happen.”
Maria says one of her favorite parts about spending time with Madeline was sharing laughter.
“We laughed a lot, and so it was really great to be with her,” she says. “It was a very pleasant time with her, very positively emotional.”
So, what does Maria’s son, Boyan, think of his mother befriending a woman he went on a date with once, two years ago?
“I don’t think I spoke with him about all this,” shrugs Maria. “He is very private, and I speak with him only on matters that he brings to the table, and he doesn’t speak too much about her … I guess they are in touch, but I don’t know the details. I don’t know anything.”
“She treated me as a friend completely independent of him,” says Madeline of Maria — though she says she has messaged Boyan about his mom and their friendship.
“He’s super aware of it … But the question I have failed to ask him so far, that I keep meaning to ask him is — has your mom ever said to you, ‘Boy, why don’t you go out with this girl again?’”
Either way the timing, says Madeline, still isn’t right: “He’s in Arizona now, I’m traveling, so once again we’re still missing each other.”
But that’s not really the point, she says. Never mind Boyan. In Maria, she’s found a friend — unexpectedly and “for life.”
“I don’t think everything has to have a Hallmark movie ending or some love story,” she says. “My love story is literally just with Maria.”
