The last thing a woman wants to do in a relationship is raise her boyfriend. In some ways, this will be inevitable. There is a fairly universal cluelessness that men are born with in certain areas -- they usually require a little coaching in sensitivity and sometimes social graces. Don't get me wrong -- some of us love to do this. With nurturing in our nature, we love to take care of our men in ways that are appropriate in a good symbiotic relationship. But when you get to the level of "stop pouting and shutting down" or "did you know a relationship involves two people?" and it's not getting any better, the age thing only weighs in on the feeling that your boyfriend has suddenly become your son.
So what's a girl to do when she's pushing 30 and the eligible men her age and up are dropping like flies? Well if you're Demi Moore, you're way beyond pushing 30 and you dive headfirst into that pool of you-could-be-my-son. Some never can break out of thinking anyone 27 and younger as bordering on illegal. And others will start to widen that door that previously only let a stray mid-20-er float through as someone who could make it on the 3-5 year plan. Only this gets complicated, because everyone has their own unspoken threshold of how old or young they will really go. And every person at age twenty-something is not at the same place of, well, emotional development (read: maturity).
I'll tell you this: There's nothing to push a single woman from 29 straight into mid-life crisis like a younger man making a jab at her age. And he's like 26. Dude, it's all relative.

Yippee-cay-ay, M.F.
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