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Personally, I'd probaby choose Penny out of both of those. You could just made two characters and romance both though. =P
With any luck, Penny will be home, too (nudge, nudge, wink, wink, if you know what I mean).
So, it's really up to you.
Emily seems to be a free thinker, and likes music and dancing.
While Penny is a sweetheart, and is the town's schoolteacher.
Their drawbacks are that Emily can be little strange at times. (Though Emily is still normal enough)
And Penny has a heavy-drinking former truck driver for a mother. (To Pam's credit, she's not a mean drinker. And in two scenes where it looked questionable, she never once even thought anything bad towards Penny.)
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So, pick whoever you feel like.
(And remember, you can always go for the other next time)
I could never marry anyone because I just felt I was being woed by Concerned Ape and I just wasn't ready for that.