The phrase share of, particularly when preceeded by a pronoun, refers to some amount that is rightfully owed to someone, or expected for someone, like when a pirate talks about his share of the treasure, or a member of a team of bank robbers talks about his share of the cash. However, the expression is often used metaphorically to refer to some unspecified amount. For example, a manager of a failed project might talk about his share of the blame.
In this case, my share of women means that the character has been lucky in love. He hasn't just had two or three girlfriends, he's had several. And when he emphasizes that by humorously adding, "In fact, I've been with like a lot of people's share of women," he means that, whatever number someone's "share of women" would be, you could probably triple that, and that's how many women the character has been with. In other words, he's a self-described Casanova.
So, the expression "I've been with like a lot of people's share of women" is intended to be a humorous way of saying that he has been in a lot of relationships with women, probably mostly short-term relationships. Yet, in spite of all this "experience," he's never felt a lasting, close, affection like Ross has for Rachel.
I've never watched Friends, but I'm guessing that these lines are meant to be both funny and touching at the same time.
I took a look at a script here and apparently, at the beginning of the episode, one of the characters thought Chandler was gay. Chandler couldn't understand why people would think that. Throughout the episode, he tries to find out why people think that about him.
Later, while complimenting Joey, another man, he realized his compliment (and possibly the way he said it) could be construed as gay:
Well, don’t we look nice all dressed up? It’s stuff like that [that makes you/others think I'm gay], isn’t it?
Edit: I just watched the episode. He was actually addressing the entire group. Still, after he complimented the group, he realized that those kinds of comments might be the reason why people got the impression that he was gay.
Best Answer
"If that" is a phrase used when someone has made a comparison (generally a comparison to something poor). "If that" means that it may be even worse than the comparison implies.
B means that the company might fall a good way short of the sales targets.
In the example "If that" could refer to two previous statements. It may refer to "This is a bad idea", and would mean that the idea is 'worse than bad'.
The second is that it refers to "This conversation is between you and me", and the meaning would be "it isn't even between you and me", presumably because Chandler didn't understand it or because he didn't say anything. In either case it's a conversation Joey is essentially having with himself.