Recently, I went on a dinner using the service Timeleft in Tokyo. For those unfamiliar, every Wednesday, Timeleft puts on a series of dinners, each made up of 5-7 strangers. Participants are matched based on a detailed survey completed within the app. This review is based on my experiences and may be different from those of other users.
Recap of My Experience
I first found Timeleft after being bombarded by ads for the app in my IG feed. I'm not sure why but for whatever reason I must have fit the algorithm perfectly. I guess it makes sense: the app is advertised as a way to meet new people in your city and hosts dinners in English and Japanese and as a bilingual expat, I fit both of these demographics.
I was interested in Timeleft admittedly for work: at Senspace, we're focused on helping people connect on a deeper level and breaking the Connection Paradox and Timeleft presented a similar value proposition with its dinners. I wanted to sign up before the end of 2024, but unfortunately wasn't able to make the time and ended up going on a dinner in the second week of January.
When the day came around to go on my dinner, I was pretty nervous. I meet people personally and professionally regularly but this felt different. The planned nature of it made it almost feel like I was on my way to my first job interview in about 8 years. Prior to the dinner I got very little information outside of some information about where people were from and their professional backgrounds, which didn't make me any less nervous, but luckily the location of the dinner was a restaurant that I'd been to before which put me a bit more at ease.
At 7PM, I went to the dinner. I was the third of six guests to arrive and the remaining guests arrived only a few minutes after me. After a brief round of intros, slightly awkward conversation turned into friendlier ones as we started to get to know each other throughout the night. Early in the conversations, I did have to lie once. I was asked why I came to Timeleft and though I was genuinely open to making new friends, I didn't want to say "to do research on this experience," so I said that I wasn't able to find much time to make friends outside of work and life at home, though this was stretching the truth.
Within five minutes, a pivotal moment occurred. The fact that I was from New York came into our conversation, and for whatever reason, so did a YouTube named, Kemio, a flamboyant model and fashionista who lives in downtown Manhattan. When Kemio came up, I hopped into that portion of the conversation: though I don't know them well, I've met Kemio a few times at events in Tokyo and New York and my wife is a big fan of his YouTube channel. During this portion of the attendees asked me politely and inquisitively, "had you know about Kemio?" For a moment I froze: answering the question by saying I know him would have been a weird flex within the first five minutes of the dinner and telling people that I was a fan of his YouTube channel would have started us down a rabbithole that I wasn't ready to go down as my knowledge about the show was little more than the bits and pieces I'd fallen asleep to with my wife. Though I didn't mind telling people that I was married, I didn't know how people might react as my assumption going in was that most people would be using Timeleft as a lower pressure way to date. I ended up making the decision to tell people that I was married and though the moment was followed by a brief pregnant pause, the dinner continued without much hubbub, with plenty of pleasant conversation.
After the dinner, we headed to a bar not too far from the restaurant: all of the participants from all of the other dates in the area also congregated at the bar, until eventually there were maybe 60 or so people there. The age range of the attendees was mostly mid 20s to mid 30s with a mix of Japanese and non-Japanese speakers. Though striking up a conversation here was not so different than striking up a conversation in any other bar, the shared context of being on Timeleft did make it a bit less awkward to speak to someone you didn't know.
I didn't stay too long at drinks as I had work to do afterwards but I did get told by one woman in her early 30s, "why are you here? You have someone to go home to. We don't!" pointing at the person next to her who was also single, reaffirming my initial hypothesis was somewhat of a dating app in disguise. The fact that no one else my dinner mentioned their significant other also supported this theory.
At about 10:30PM, I walked out into the Shibuya night, proud that I have done something new and ran back the night in my mind, thinking about the value of an app like Timeleft.
Reflection on the Experience
What I liked
I made one friend!: This is one of the goals of the app and I achieved it. There was one person in the group that may not become my best friend, but already invited to an event I put on a few days later.
Small group setting: Though to be honest, I didn't feel like my passions overlapped that much with the rest of the group, it was still an easy setting to get to know everyone else with 6 people in our dinner. 6 was just the right number of people to be able to speak at least a little bit to everyone.
What I didn't like
Feel it's still a dating app in drag: I feel this is presumptuous to say as I didn't get to talk to everyone, but I still felt like I was on a dating app. This is in large part because of the fact that you're on a group dinner date/going to bar. Maybe if you went to an art show, go on a hike, play sports together or create something together, then you might be able to see different sides of the people you are with and connect on a deeper level, but group dinner and drinks only allows you to meet vs. connect, especially with the number of people.
Randomness of Matching: On paper, our dinner probably looked fine, but in practice the matching was not great. I didn't feel my interests overlapped with the group and also felt that a mutual friend with anyone in the group would have gone a very long way towards establishing a level of comfort.
No community layer in app: After you finish the night, you review your fellow participants and match with them one by one vs. getting connected as a group. This further pushes my theory that this is a dating app in drag and if Timeleft is a dating app, then the goal is to get off of the app vs. stay on. Without staying on, there isn't an opportunity to form around the application.
P.S.: People don't proudly say, "I'm on Tinder!" or "I'm on Hinge!" because of this lack of community layer. Understand that maybe Timeleft is potentially not too focused on this portion of the relationship value chain (it's a lot to manage the initial meeting and maintaining the relationship) but think this could be problematic for sustainability for the app long term.
International party vibes: Tokyo has what are called international parties, which are an opportunity for English speakers (of Japanese and foreign descent) can meet and mingle. When I first got to Japan in 2026 I went to a few of these events, but ultimately stopped as simply speaking English was not enough of a filter for connecting with interesting people. The bar event at Timeleft gave off similar vibes: every conversation just felt very random in a way that was somewhat offputting and if anything, I felt like I wanted to go back to the smaller group setting.
Would I use the app again
Maybe to meet people in a new city, but likely not in any other case. And even in a new city, considering if I'm traveling I'd likely be with my wife, I'm guessing I won't ever use it again.
Thanks for reading my review and would love to hear more about other people's experiences on Timeleft too!
