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Originally Posted by need4speedo
...a pair of J.Crew swim shorts. Ugh. While they're short and expose plenty of thigh, her intentions are clear that she wants me to give up the speedos. She has never truly embraced my preference for wearing them, but has tolerated them up to a point. We'll be going to Aruba in September and I'm not sure if she was expecting me to wear these short shorts while we are there. It's Aruba, I'm not giving up my speedo freedom while I am there. If there's any place to wear them, it's there!
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None of us knows the details of your situation but you may be reading too much into this. Maybe this is a suit she is comfortable with you wearing around her conservative family and friends. Why would she buy you a suit in July that she wants you to wear in September? I’d be open and just tell her you noticed that she got you a new pair of trunks and allow her to speak her mind.