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During season 5 of Shameless, Fiona is working at Patsy's Pies. The place regularly gets visited by a woman who leaves exceptional tips, and displays a special interest in Fiona:

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We find out she is send there by Jimmy 'Steve' Lishman - known to the woman as Jack - who sits across from her when he reintroduces himself to Fiona.

Somewhat dissentingly the woman, Angela, says "I'll let you two catch up", and leaves the place.

Why was Angela in cahoots with Jimmy; what part did she play on Jimmy's behalf in relation to Fiona?

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I think that Jimmy has explained this:

Angela is his partner in crime, and although it is not explained what is he doing right this moment (or at least I don't remember that - it is irrelevant anyway), it seems that he can trust her enough to check on Fiona, his ex girlfriend.

If you remember, Jimmy was forced to abandon Fiona when he got in serious trouble with mafia - he was basically kidnapped without any chance to leave message to her. He is now too scared to just simply pop-up and say "hi" - while he might be still on the run from the mob (judging by his shady behavior), what he is really afraid is Fiona's reaction. But since he still has feeling for her (and he hopes that so does she), he has asked his "friend" Angela to check on Fiona, while he was trying to gather courage to show up in person. Coincidentally, Angela has managed to develop a small crush on Fiona as well, hence she might be doing this "checking" a tad too often...

This small plot goes really nowhere:

Angela tries to flirt with Fiona but is gently rejected, so she helps her instead to meet Jimmy/Steve/Jack. Fiona eventually rejects him as well. Both criminals disappear from the series.

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  • Eventually though, he is still just popping up to say "hi" (possibly because Angela was unable to take her somewhere; a place where Jimmy would feel more at ease?). My problem is that - although Jimmy always seems to want to do things on his terms - there is not really a reason for 'recon'; he can stalk her as he has in the past, he can approach one of Fiona's siblings, &c. Unless he expects people are waiting for him, realizing he might come back to Fiona - that indeed sounds like the most logical explanation. Thanks for the answer!
    – Joachim
    Oct 20 '20 at 8:43

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