Idk she probably had to remind him not long before that episode that when she's showing signs of insecurity about her looks it would be nice affirm her by telling her a compliment or something like that. Although that could be too complicated for simple ian so maybe something like that but in simpler instructions. And I do not believe that he's ever bought her anything without her putting idea in his head or straight up telling him to buy specific thing. That includes that birthday cake and also cruise tickets and also the engagement ring as in she 100% suggested if he does not propose she's leaving. He's too cheap and socially retarded to think of any of these things on his own.
He chose bad moment for the compliment bc she just wanted everyone to confirm she totally did look like maxmoefoe which lol what a throwback. It was a thing yaoi-loving idubbbz/cancer crew fans used to say in ~2017 to cope with the fact that neither ian nor max were totally gay for each other. "Okay now ian has a gf too but doesn't she kinda look like Max tho?? Omg he's so in love with Max that he found a female clone of him!! uwu" I've never seen the resemblance and found it cringe as hell but it made a lot of idubbbz fangirls instantly love her for that thing alone.
