Kara Danvers (Melissa Benoist) has had fights and falling-outs with her friends before, but nothing has shaken her as much as Lena Luthor (Katie McGrath) spitting in the face of their friendship and working with Lex (Jon Cryer). In the 100th episode of Supergirl, Kara will have a chance to do things over in an attempt to fix things with Lena, but it won't be as simple as she thinks.

The road to a repaired friendship with Lena means Kara revisiting scenes, and people, from her past, courtesy of Mxyzptlk (Thomas Lennon). One such familiar face is Winn (Jeremy Jordan), back for a bonus adventure after his two-episode arc that saw him facing down his old dad-shaped demons. TV Guide spoke to Jordan ahead of the landmark episode about what it was like to be back, whether he thinks Kara and Lena have a chance at patching things up, and why he kind of hopes they don't.

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Oh, and we definitely asked about his next potential return to the series and whether music will be involved. Check out what Jordan had to say below.

Jeremy Jordan, Supergirl Photo: Katie Yu, Katie Yu/The CW

First off, what was it like returning to Supergirl for these three episodes?

Jeremy Jordan: It's been wonderful. I mean, I call it kind of like a two-episode arc with a bonus episode attached, because I have my sort of thing and then the hundredth [episode], which is its own beast. But it's been it's been really great. I love being back and hanging out with the cast and crew and getting to have some really fun stuff, and some new stuff, which is really great — getting to revisit a character that I built years ago that I started to love was really lovely, and I had a great time.

Is there any chance that we'll get to actually meet Winn's wife and kids from the future?

Jordan: I mean, sure, why not? I'll be down for that. I don't know who they had in the picture. I think they were just photo doubles. This was the first that I knew that he had any sort of wife and kid in the future. His wife is a superhero in the Legion, so I wouldn't be surprised if the next time he comes back, he doesn't come back alone — and I hope there is next time he comes back. I told [them] that I'd be more than happy to return again.

The photos from the 100th episode are out and we know Winn is in his Legion suit. Is there a chance we'll see old-school Winn from before he went to the future, though?

Jordan: It's hard to say, because I don't think that new Winn is really any different than old Winn. When we first met "New Winn" he was very upset and having to deal with all this drama, but then as the couple of episodes that we have seen aired progressed, we started to see glimpses of our old friend. I don't think that he's ever going to change too much. We call the Toy Man version like an evil version of Winn, [and] the route that he could have taken, but we decided a long time ago that he wasn't going to be that person. In the hundredth episode, you're definitely going to see glimpses of our old Winn for sure, [but] it's not like we haven't already seen those, as well.

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The premise of the 100th episode is that Kara wants to fix her friendship with Lena. What advice would Winn give her to make that happen?

Jordan: One of the fun things that I've decided, that I liked playing in the first two episodes when I came back from the future, was that Winn has sort of insight on how all this stuff shakes out. Of course, he can't really say or really tell what's going to happen; but if you really watch and pay close attention, you'll see [his] reactions to certain things that happen, how he handles new information, how he sort of gives advice, trying to sort of guide, especially Kara, towards something that he knows from the future is going to pan out in a certain direction... So, being back from the future, if he was to give her advice about Lena, it would be to say kind of what he already told her, which is, "Just give it time." If Lena ever wants to come around, she'll come around. I think Winn believes in the power of friendship over anything else, because it's really stayed with him. It's really been a major factor in both his and Kara's lives. I don't think that he underestimates the intrinsic, built-in nature of real friendship.

Does that mean that you, Jeremy, are rooting for Kara and Lena to make up, or do you want to see Supergirl face off with her own Luthor?

Jordan: I personally would love to see Katie be like as evil as humanly possible because I think that would be really fun, but that's just the Jeremy, watching my friends on TV version. I think that Winn definitely wouldn't want that. I don't know if anybody in the Supergirl world really wants an evil Lena Luthor because she could be very formidable.

Have you formally pitched how you'd like to return to the series later on?

Jordan: I usually leave that sort of stuff up to [the producers]. It would be fun to see a little bit of the future, I think. I don't know how economically possible that is. I always thought that would be cool. I think it would be cool to bring back some of the Legionnaires.

I will also put this out there: It's been a while since we've had a Supergirl musical episode.

Jordan: Well, we've never actually had a Supergirl musical episode. We only had a Flash musical episode. Listen, I'm down for it. It's quite undertaking as I recall, logistically, but [it's] certainly possible. If they did it, they would certainly have to schedule it not anywhere near the crossover, to give everybody a break. The superhero world always has fun ways to get into those sorts of things. They may have been used before, but I'm sure the other avenues into a musical episode... One of the reasons that I did the show was to kind of escape everybody [seeing] me as like the musical guy. But you know, I did the show for a few years, so I'm more than happy to sing and dance a little bit.

Supergirl's 100th episode airs Sunday, Feb. 23 at 9/8c on The CW.