The letter says: "[...] It's been almost 20 years since we've seen each other, but now there's something I need to tell you. Years ago, after our story ended, I discovered I was pregnant. I decided to go through with the pregnancy and I had a baby. A son. Your son. I decided to raise him by myself because our time together had come to a close. My son is now almost 19. [...]"
For him to remember back 20 years and remembering when exactly he saw each of them last is probably not easy. Him being a ladie's man doesn't help. And since it's "almost 19" and "almost 20 years ago", it does leave room to stretch over months.
And some of the womens responses lends credibility to him having slept around as well. Even 'today' in the movie, where Murrays character is getting older, he still has a few ladyfriends. -That may or may not be true though, as it is only expressed through other's opinion of him and his life.
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