To do I owe you a beer, you need 40 likes and one heart. I need to verify this, but maybe if you have two hearts it doesn't trigger, or is as you said and you can't do it after the new event.
That's the working theory right now that the "owe you a beer" needs 1 heart to trigger and since the new event with Logan gives you a heart it locks the player from doing the "owe you a beer" after it