Ten Dates

Toni is a potential date for Ryan.

If you have already completed one playthrough you will be able to choose which person you want to try and date, so you can select only Toni to speed up this achievement.

Here's everything I did to earn the achievement.

Second profile pic.

Industry: Other.

Interests: Sports & Fitness, Charity, Food & Drink.

Star sign: Taurus.

> Defender.
> Father.
> Keep listening.
> The man's son.

Like the last two pictures - one showing Toni and a man I assume is her father, the other showing the goalposts on the football pitch. I can't say for sure how much these impacted the outcome, but those are what I selected.

Toni will accept the request for a second date.

> Can I help?
> Dare.
> Show off your secret talent.
> Truth.
> Professional.
> Grossest food combo.
> Dare.
> Supportive message.
> Learn more.

Toni will agree to a third date. Here's the dialogue choices to get a successful result:

> Jock.
> Remain.
> Accept.
> This card.
> Accept.
> Accept.
> I like you.