According to a July survey by travel platform Skyscanner, 47 per cent of Singapore travellers rank taking their first holiday together as the most exciting relationship milestone, outpacing first kisses at 27 per cent and holding hands at 21 per cent. Skyscanner polled 1,000 Singapore respondents, while dating application Coffee Meets Bagel surveyed 380 of its local users to examine how shared travel tests compatibility.
Relationship Milestones and Travel Preferences in Singapore
Taking a first trip with a significant other outranks traditional romantic milestones for modern couples. Skyscanner’s July data reveals that nearly half of local travellers view a joint vacation as the ultimate early-relationship test. This sentiment overshadows physical milestones such as the first kiss, which secured 27 per cent of responses, and holding hands, which drew 21 per cent.
The polling sample comprised 1,000 Singapore respondents. Roughly 41 per cent identified as single, 39 per cent as married, 16 per cent as currently in a relationship, and 3 per cent selected other categories. These figures demonstrate that the appetite for travel-tested romance spans across varying relationship statuses.
Did you know? According to Coffee Meets Bagel data, roughly 56 per cent of Singapore users are more likely to initiate a conversation with someone who features a travel experience prominently on their dating profile.
Testing Compatibility Through Shared Travel
Around 90 per cent of Coffee Meets Bagel respondents note that a trip does not automatically guarantee a partner is “The One,” but it does clarify whether the relationship has a viable future. Amanda Chong, dating trends and insights lead at Coffee Meets Bagel, points out that travel shifts a connection from simple chemistry to actual compatibility.
“Travel introduces dozens of tests in the form of shared decisions and unexpected situations—from planning an itinerary to discussing budgets to dealing with delays or changes,” Chong says. Those high-stakes moments show how two individuals communicate, compromise, and support one another under pressure.
Real-life examples underscore this shift. Content creators Natasha Conceicao, 29, and Erwin Chong, 32, matched on Coffee Meets Bagel in 2019 and booked a trip to Bangkok just four months later. Erwin Chong notes that travelling uncovers personal quirks, while Conceicao adds that a shared trip acts as a snapshot of what the next 50 years might look like.
Seasonal Dating Trends and Holiday Planning
Dating momentum in Singapore often shifts with the calendar. Cyndi Hui, travel expert at Skyscanner, explains that 47 per cent of local travellers feel more open to starting a relationship in the second half of the year as festive periods and year-end leave arrive.
“By the second half of the year, there is likely to be more clarity about work and some leave days to clear,” Hui states. “There are also festive seasons coming, like Christmas, New Year’s, Chinese New Year and Valentine’s Day. One of the reasons people may want to get into a relationship is to have someone to celebrate festive seasons with.”
Top Asian Destinations for Couples’ First Trips
When couples finally book that inaugural getaway, they predominantly lean towards regional Asian hubs. Skyscanner data highlights Tokyo as the clear favourite, capturing 39 per cent of the responses.
- Tokyo: 39 per cent
- Seoul: 26 per cent
- Taipei: 24 per cent
- Bangkok: 19 per cent
These destinations offer a mix of structured transit systems and diverse cultural itineraries, making them manageable testing grounds for newly formed partnerships.
Pro Tip: When planning a first holiday together, keep a flexible itinerary and discuss budgets openly beforehand to minimize friction during unexpected delays.
Frequently Asked Questions
Does taking a trip together guarantee relationship success?
No. According to Coffee Meets Bagel, roughly 90 per cent of respondents state a trip helps determine compatibility rather than guaranteeing a long-term match.
What is the most popular first holiday destination for Singapore couples?
According to Skyscanner, Tokyo ranks first at 39 per cent, followed by Seoul at 26 per cent.
Why are Singaporeans more open to dating in the second half of the year?
Skyscanner expert Cyndi Hui notes that job leave clarity and upcoming festive seasons drive increased openness to romance during this period.
What are your thoughts on taking a holiday during the early stages of a relationship? Share your experiences in the comments below, or subscribe to our newsletter for more travel and dating insights.
Worth a look