You're in a relationship. You're having an awesome time. But now, the feelings are starting to get intense, and you're wondering when to say I love you. 19 guys talk about when they knew they were ready to say I love you, how they knew they were ready to say I love you, and how they said I love you for the first time. I spoke with relationship expert and host of the breakup BOOST podcast Trina Leckie about when it's OK to say "I love you" for the first time in a … 6 Signs He's About to Say I Love You. "The regret of my life is that I have not said 'I love you' often enough." — Yoko Ono. Is there a right time to do it? ... it's nerve-wracking to be the first one to say "I love you."