Poisoned Purple Pen

I have a dilemma

I've cruised my way to chapter 11 of APF, and now I'm trying to figure out just where Grant should make his entrance, where he can have the most collateral damage, that is.

Backstory: Ten years prior, Anna was dating Nolan for a month. Grant sweeps into town, has the hots for her and lies about having connections in the fashion industry back in New York. Being young and naive, Anna runs off to New York without a word to her friends and family. Once in NY, Anna quickly learns of Grant's lies, but is too ashamed to go back home and spends the next decade alone in NY going nowhere.

Now: Anna and Nolan are fighting the attraction, but losing and resigning themselves to try again. Anna just got a new job at a boutique and her boss likes her designs.

Dilemma: Should Grant
a) Come into the Boutique and sell himself to Lisa, Anna's boss?
or
b) have a public entrance where both Nolan and Anna are?

I can't decide which would be worse for Anna. Just Grant's reappearance will cause trouble for her. Since Nolan already believes she'll never stick around is having trouble trusting her, option B would work. Her new career is just taking off, and having him try to manipulate her boss would definitely have a major impact on her as well, so option A could work.

Sigh, I just can't decide.

I'm open to suggestions!