I found Why I Dress Up For Love to be a disappointment. The main problem I had with this drama is that it never felt like the female lead was making choices for herself, but rather that she was just going along with what the male lead had to say. The drama, and the male lead, paint the changes the female lead decides to make as her decisions. This is what she wants. But the male lead is the one doing all the driving. He constantly critiques the female leads career choices, making frankly kind-of hurtful and selfish comments about how she lives her life. I think it's clear that we're not supposed to take his comments in the way they come across. He's not intending to be hurtful or dismissive. It's actually part of an intentional character flaw. He's not very good at expressing himself, and he has his own baggage that informs his opinions. But even though the writers aren't intending for him to come across as a bit of a jerk, that's still how he comes across.

What the writers were trying to convey to the audience was that the female lead wants more for her life, that she's not pursuing the things she really wants to, and the male lead is pushing her to try for more. But when all of the female leads questioning over her career and her future happens only after the male lead has made another hurtful (although unintentional) comment, it's not going to feel like the female lead has genuine uncertainty about her life choices. It's going to feel like the male lead is a bully making the female lead feel bad about herself, which is the last thing you want in a romance.

For myself, I don't dislike the male lead. I actually quite like him. You can tell he's been hurt by life and that hurt informs much of how he interacts with others and the choices he makes for himself. You really just want him to be happy. But I didn't appreciate the writers pretending the female lead was at the wheel of her own life when they've played the story out in a way where all of the changes she makes happen only after the male lead tells her she should make them. I do like that she decided to pursue being a purchaser, because that did feel like something she genuinely wanted, and we do see how running her Instagram account takes a toll on her, but we needed to see more of an internal/external struggle. More unprompted self-reflection, more difficulties at her job, more something to convey to us the viewer that she really is genuinely questioning her life path and not just trying to please a guy she's not even in a real relationship with.

This leads me to the second male lead and my other problem with this drama. The second male lead never even puts up a fight! It becomes clear at a certain point that he has feelings for the female lead, and he even seems to want to act on them, but he never, not even once, truly enters the ring. He makes a couple 'declarations' to the male lead about 'If you don't go for it, then I will,' but he never follows through. It makes him come across as weak and mealy-mouthed. Which again, I don't think was the writer's goal, although I'm also not sure what their goal was with him. But just like the male lead, I actually really like the second male lead. He's very good at his job, seems to have strong morals, and he definitely values and appreciates the female lead. I kept hoping he would become a real contender for her affection. Honestly, part of me wanted the two of them together instead. There was something about their potential romance that just felt a little bit electric. But he never rises to the challenge, and this leaves him as a disappointing, and somewhat useless, character.

Ultimately, all of these problems with the central romance/love triangle are a flaw with characterization, not with the characters themselves. All three of them are likable people on their own, and both romantic pairings are compelling in their own ways. So if you can overlook the missteps and see what the writers are trying to do with the story, then you'll be able to enjoy Why I Dress Up For Love. Personally, while I can see what they were trying to do, and I can appreciate the attempt, the execution left me disappointed.