Ten Dates

I did this in my second playthrough. The game will let you skip already seen scenes, plus let you choose only one person to speed date. From the main menu, here's what I did:

Select New Game
Select Misha
Fill out your bio however you want, just click through it

Press to skip already seen cutscenes

The game will now let you select your speed dates
Select Ty (and only him)
Select Start

Select "Ask"
Select "Not cool"
Select "Yes"

Achievement will unlock after the cutscene.

Once you have completed one playthrough with either Ryan or Misha the game will then allow you to select which people you want to choose to try and date in subsequent playthroughs. You can use this to your advantage for specific achievements by selecting one person to date and aiming for their achievements.

To help speed up that process, you can also go for this achievement in your first playthrough, having no successful speed dates.

Alternatively, if you've already completed your first playthrough you could select one of the below prospective dates on their own and follow the choices to put them off.

Here's how I did that:

Select Misha. Set up her profile in any way you like.

The order of the dates may differ for you, so check below foe each one.

Bash

> Press.
> No nickname.
> I don't want to know.
> Yes.

Lucas

> Share.
> No.
> Don't need tech.
> Change subject.
> Extrovert.

Jake

> No.
> Yes.
> Don't know yet.
> Keep listening.
> Young adult.

Ty

> Ask
> Not cool.

Hazel

Following the dates with the men, you'll meet Hazel at the bar.

> I'd never.
> Don't watch.
> No.
> No.
> Move on.
> Disagree.

You will then bump into a guy in the hallway.

> Yes.