Roscommon Romeo ‘boomerangs’ back to First Dates

Roscommon Town man James Kilmartin made it back to First Dates Ireland on Thursday night and this time he was armed with more puns than the maître d’ could handle.

James, who first graced the First Dates Ireland restaurant in 2019, made a triumphant (and slightly cheeky) return on the latest episode, aired on Thursday night.

“I’m a boomerang — I always come back,” he declared, proving that while love may be elusive, his sense of humour is very much intact.

Viewers may recall James’ first appearance during series four, when his date ended with a hopeful-but-short lived “yes.” Now, several years and many dates later, James was ready for another shot. Or as he put it: “The first time was the starter — this is the main course.” This time, the Roscommon native was paired with Joseph, a 39 year old originally from the Philippines who also works in tech. The two bonded instantly over their mutual exhaustion with dating apps — and their mutual admiration for Mateo, the ever graceful maître d’. James even admitted: “I’ve been on more dates than Mateo.” From there, things flowed more smoothly than a perfectly poured Sauvignon Blanc. The pair chatted about life, tech, artificial intelligence, and their shared enthusiasm for diversity and inclusion. It turns out romance isn’t dead — it’s just really into data-driven conversations.

By the end of the meal, sparks were flying brighter than the fairy lights behind the bar. Both men said a confident “yes” to a second date, with Joseph describing James as “smart, sincere and a tender soul.” Their night didn’t end at the restaurant either — they headed off together to Copper Face Jacks.

In true 2026 fashion, the show later revealed that their second date was “planned by AI.” Whether artificial intelligence can outsmart Cupid remains to be seen, but for James, returning to the First Dates restaurant might finally have paid off.

Stay tuned — Roscommon’s favourite boomerang might just have found a place to land.