(2nd alternate definition to guylemma)
Guy trying to please his SO fails regardless of what effort he puts forth. Fellow can't decide which direction to go because he's damned either way.
Bob: Hey honey, look at the cute yoga jacket I got you from that new shop!
Betty: Umm, you said you'd be home early and you were shopping?!
Bob: But, but... ugh, what a guylemma. I was shopping for you!
Betty: What did you say?
Bob: Dude, hey, I'm not sure what yoga jacket to get my wife. I think she wears a larger size than this, but if I get her the XL, she'll think I think she's fat.
Dude: Whoa, quite a guylemma you're in there my brother. Damned if you do, damned if you don't.
Relationship trouble with a boyfriend or husband.
Stemming from the words guy and dilemma.
She's not coming out tonight, she's having a bit of a guylemma.