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From Friends(a very old American Show) Season 02, Episode 201

Context is that Joey came to talk with Rachel, and told her he could understand her misery. To let Rachel believe he did know her feelings, he said the following words:

I've been with my share of women. In fact, I've been with like a lot of people's share of women. The point is, I've never felt about anyone the way Ross felt about you.

From the dictionary, I learned that be with you / me means to understand what someone is telling you or explaining to you, but how to explain my share of women? What's the meaning of the whole sentence?

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    I am pained by the characterization of Friends, which opened when I was 46 and closed when I was 56, as "very old". The first American TV sitcoms were adapted from radio in the year before I was born; a "very old" one would be one which played in my childhood. So learn some history - and Get offa my lawn!! :) – StoneyB Jan 26 '14 at 15:08
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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.

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I'm guessing. It must have been Chandler or Joey who said that. Perhaps, Joey. He thought of people's share of women as all women in the world. "Being with his share of women" would mean being with women he had been dating with.

So,

I've been with my share of women. In fact, I've been with like a lot of people's share of women. The point is, I've never felt about anyone the way Ross felt about you.

is what Joey (or Chandler) talking to Rachel. What he wants to say at that time is that, in his own experience with women (which is "like a lot", according to him), he has never been as serious about anyone as Ross is serious about her.

In short, he sincerely think that Ross really loves her.

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