Tails: The Backbone Preludes – How To Successfully Flirt As Howard

Quick Links

  • Who To Flirt With
  • Flirting With Niles
  • Flirting With Freja
  • Flirting With Wisconsin

Howard, one of the four protagonists of Tails: The Backbone Preludes and the sole protagonist of the next game in the series, Backbone, is a photography student in this game. In his second chapter, we find him and his roommate Larry after a night of drinking, with Larry betting that Howard is a terrible flirt. Inevitably, this leads to the chapter's challenge: flirt successfully.

This is a fun, short sequence that has you hitting up your choice of three different eligible students that you share a hallway with. It's quite easy to mess these conversations up, though – you'll have to be your most charming self, and adapt your responses to the personality of your intended lover.

Who To Flirt With

There are three people you can flirt with to comply with Larry's request – Freja, Niles, and Wisconsin. They are all located in the hallway outside your room, and each of them will require different tactics if you want to be successful.

The sections below contain examples of perfect conversations for each of the three potential flirting targets. As Tails is a slightly randomized game, these are not exhaustive and you may encounter slightly different conversation topics – just make sure you follow the tips for each individual. If you're concerned about not getting the perfect flirting experience and getting the achievement, save beforehand.

You cannot flirt with Larry. You can try to, but it will just lead to some general hints about how to flirt with the other people that you actually can flirt with.

Flirting With Niles

Niles is a very cool customer. When flirting with him, you'll want to come across as very confident – Niles doesn't appreciate it when you avoid his questions entirely or beat around the bush. In fact, turning the conversation on him and interrogating him about himself is a good way to get him interested. Things to avoid are being obnoxious and making sexual jokes.

Niles's Dialogue

Correct Response


A little derivative, but effective.

Are you trying to flatter me, Howard?

I bet I can do more than flatter.

But your confidence is admirable, however mispllced.

Shut your mouth and let me flirt, idiot.

Let's see what you've got.

What I've got? You're looking at it.

Do I strike you as the shallow type?

Are you saying physical attraction is unintellectual?

But I would say that physical attraction is nothing unless backed up by an interesting mind.

Pretty sure I've proved that already.

That's not a one-and-done, Howard. But I dig it so far.

So I'll keep proving it. Go on, try me.

I don't want to be caught in an echo chamber.

In other words, you prefer to have the sole correct opinion in whatever room you're in.

Why so aggressive?

Because it'd do you good to have to explain yourself once in a while.

I'll make an exception for you.

For me? That's sweet.

How do you plan to move things forward post-flirt?

Oh, I'm done. Next step is that you come to me.

You're assuming I will.

If you're interested, then yes. That's the whole point.

You make a good point. Maybe I will.

You most certainly will. I know it.

I guess we'll see, Howard. Not a bad approach.


You're, well, interesting. Very interesting.

You said so already. You're not flustered, are you?

Flirting With Freja

Freja will see right through any attempts to flirt with her, but you can still make a good display of your moves with her. The key to success with Freja is being charming and interesting, not rowdy or boring. She appreciates dorky humor, but not sexual humor. Go for the classic, charming, and fun approach and you should be on to a winner.

Freja's Dialogue

Correct Response

Howard, are you trying to flirt with me?


If you wanna show someone a good time, you have to BE a good time!

How would I do that?

You and me, we're going to workshop it. Fix you up into a lean, mean, flirting machine.

Can I be a banging machine? I'd rather be a banging machine.

I'm an artsy cutie and I think you're cute. WHAT do you say?

I say I'm a photographer, and I want to take a picture of you.

Oh? Just a picture?

Hey, I'll take as many as you'll let me!

What, you're expecting to get to take more than one? What makes you think that?

You're a great subject.

What next, huh? What's your next move?

Probably invite you to meet up? Take some pictures?

There's hope for you yet, Howie.

No one has ever said that about me before. Thank you.

Next up: for the sake of practice, hit me with a pickup line. What do you say?

Hey, are you a branch? Because you can stick with me anytime.

That is… really stupid, Howard.

Should I spruce it up?

Are you just going to keep giving me tree puns?

Guess I'm in a sappy mood.

It's got that disarming charm to it, I guess. You pass.

Very gracious of you. What's next?

The party is slowing down and neither one of us have plans. What do you do?

I'm starving – you want to get some salted nuts?

It's chill, it's relaxing, and it's public. This is the move, my man.

So, uh – you wanna get some nuts right now?

We're workshopping it, remember?

…But what if it wasn't?

Look, man – I think you're pretty cool, but at the end of the day, you're just not my type.

You know what? Fair enough.

Flirting With Wisconsin

Flirting with Wisconsin is a pretty subtle ask. You need to be earnest, friendly, and honest with him, making him know that he's liked. Avoid being too sexually forward or making overtly flirty remarks – the slightest hints toward liking him as more than just an RA will be enough to seal the deal. Getting him flustered and then bringing him back down with earnest plan-making is the key to getting Wisconsin to fall for you.

Wisconsin's Dialogue

Correct Response

W-wissie? Did you just give me a nickname?

…Should I not have?

That's, uh… I like that!

Well, Wis? You never told me how it's going.

You know, just doing my best!

If you ever want any help, you know where my dorm is.

We could, um, like, organize sheets together?

Sheets, huh?

Unless, like… no, nevermind, I mean paper sheets! Spreadsheets!

I'm just messing with you, man, I like you.

I, uh, I think you're a pretty cool guy too, Howard.

We should hang out more, man.

I don't really feel like I get many moments to myself nowadays.

Don't worry, man. I'll help you relax.

How come you're so talkative today?

Honestly, I just want to get to know you better.

So, um, have you been doing anything… fun lately?

Nothing comes to mind. What would you suggest?

I like to, uh, go there and just relax. Or make notes.

Can I come with you sometime?

I'd – yeah, that'd be awesome! I can bring juice boxes!

As long as you're there.

These notes won't take themselves!

You got it, Wissie.

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