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sounds like the ex is a loser. from the ladies i've talked to, confidence is one of the bigger qualities that initially attract them to guys. pining away and plotting schemes to win back girls when it is over verges on pathetic... and pathetic is not a strong and secure place.
now if she is into the ego boost that she gets from having this guy obsess over her, that's something you should be very wary of. bail now, there are plenty of fish in the sea and you sound like you've got plenty of time for fishing.
never give anyone an ultimatum. it's the relationship equivilent of getting into a land war in asia. never punch out a ex unless he swings first and there are witnesses to vouch for you.
but, if you are going to hook him up with a skank, get it on video. even if it backfires on you in your relationship, you'll have great material for revenge on the guy who started the problem.
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if everyone is thinking alike, chances are no one is thinking.
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