I (27F) can’t tell if this man (40M) is just incredibly generous or slowly pursuing me. How do I decipher him?
This has been going on for about a year. Sorry it’s long.
I 27F run a small bakery by myself. I make custom cakes, serve coffee and desserts, and also supply desserts to a few cafés.
A man 40M (maybe late 30s, early 40s) first became a customer by ordering birthday cakes. Later I found out he owns a fairly large restaurant and asked if I’d supply desserts. I agreed, and that’s how our business relationship started. It’s been a year. Maybe a little longer.
One thing I found odd from the beginning, I told him I don’t do deliveries, and instead of sending an employee or driver, he personally comes to pick up every order himself even though he’s the boss.
He follows my personal Instagram, and after I posted stories while traveling over Christmas, he started replying. At first it was just casual conversation, so I thought nothing of it.
After Christmas he brought me souvenirs from his own trip. I happily accepted because I thought it was just a kind gesture, it was mostly snacks. Then the gifts slowly became bigger and more personal. I started feeling obligated to give something back, so I’d usually give snacks for his kids.
Last winter I was burnt out, lowkey depressed and closed my bakery for 3 days. He checked if I was okay, then told me he’d brought me things from Korea. I went to his restaurant with my mom, getting dinner and then getting whatever he brought. He remembered I loved salt bread. It wasn’t just bread, it was skincare too.
He even asked his son, who was visiting Japan, to buy me souvenirs despite not going himself. It wasn’t generic stuff either, he got me a Gojo (Jujutsu Kaisen) figurine after apparently noticing a Gojo shirt I’d worn before, plus merchandise from the Osaka Expo.
Around this time he also started replying to my stories I posted and sending me Instagram reels. I used to reply, but eventually stopped because most were really not funny. He still sends them regularly even if I only react with an emoji or don’t respond at all.
A few weeks later he told me he’d left something at his restaurant for me. It turned out to be more skincare, snacks, and a Tamburins fragrance oil and bag charm. Even I know Tamburins isn’t cheap, so again I felt grateful but also burdened.
Earlier this year I closed my bakery for three weeks to attend a bakery expo in Europe. He asked if I’m on a specific flight, it turned out we were on the same flight. He offered me a ride to the airport, i accept because my family couldn’t take me. I assumed he’d be traveling with family since he has kids, but it was just him and his driver. At the time I still viewed him as an older brother type who was simply supportive of my business.
I thought we’d part there, but he invited me into the airport lounge, bought me lunch during our layover, checked on me several times during the flight, and even sat beside me for a while because there were empty seats.
While we were both traveling he’d send me updates from his trip (food, scenery, his kids), and he’d continue replying to my Instagram stories.
When I got home, he gave me another gift, a custom hand tufted rug with my bakery logo. I knew it probably cost around $200-300, because I asked the exact artist before but felt it was over my budget. I thanked him but also told him he really didn’t need to buy me things. He brushed it off as “an investment for the cafe.” The rug is now hanging in my bakery.
Then came the part that actually made me uncomfortable.
He suggested I join Pilates because I work too much. I politely declined and said I was busy.
A week later the Pilates studio called me saying my place had been reserved. He had given them my phone number without asking me first.
When I told him I was uncomfortable with that, he apologized immediately and said he didn’t have bad intentions. He said he knows I’m introverted, thought I might get lonely working alone all the time, and just wanted me to spend time doing something for myself. I told him I wouldn’t be going.
Most recently he was traveling abroad again and asked if I wanted anything from London. I said no. He replied that he’d bring something anyway. I told him again that he really didn’t have to. Two weeks later he came back with another bag of gifts. Not random souvenirs either, things that were incredibly personal: a Lotr tea towel, Ghibli merch, baking ingredients that are difficult to find here. Basically all things he knows I like.
The confusing part is that he has never made me uncomfortable in person.
Whenever he comes to my bakery, he’s polite. He talks about work, buys coffee or picks up desserts, and leaves. He’s never flirted, touched me, made inappropriate comments, or tried to corner me.
It’s everything outside of that, the constant messages, remembering every little thing I like, and especially the gifts after I’ve repeatedly said they weren’t necessary. It just keeps piling up.
I don’t dislike him and I don’t think he’s a bad person. I just feel like the relationship has become much more personal from his side than from mine. Idk if it’s just genuine support or if he’s pursuing me even if he’s taking the long way.
I saw him as friendly at first, when i told my sister she said he’s interested in you bc no man is going to buy you so many gifts without ulterior motives. I genuinely don’t know if he’s married, divorced, or single because he’s never mentioned, but he definitely has 2 kids.
I’ve never dated, so this kind of attention is confusing me. I hate confrontation , i don’t want things to get awkward.
Tldr:
A restaurant owner I do business with keeps giving me expensive, very personal gifts, remembers everything I like, messages me often, and has crossed a few boundaries despite being perfectly respectful in person. Am I reading too much into it, or does this sound like someone trying to pursue me
Posted Aug 3, 2026, 1:50 PM UTC