Vanessa

Vanessa Eddy's mom, a rather strong independent woman and definitely one thicc MILF.

You can interact with her while having bum or normal look, but you'll only be able to progress with her while having a normal look. She's a little rough around the edges, so most typical wooing methods won't work on her - you'll need to show strength and interest.

Gift preference: a box of chocolates

Stage 0: Introduction

You can meet her at the beach on Wednesdays after 11:00, you can ogle her, then select:

"Hi..." > "It's hard to pass by such a beautiful woman! My name is..."
"I like curvy women! It's hard not to notice you!" (timed choice, be quick)

She'll shoot you down immediately afterwards, but at least you'll get her attention.

Stage 1: Mama's boy

In order to progress with Vanessa, you need to know Eddy, hence have completed Maria's S1 Route 1 where you hang out with Diego and meet Eddy and Sandra. Also, make sure you have your Energy at max before starting this quest, since you'll get into a scuffle with Eddy.

Go to Eddy's place (a hidden marker near the motorcycles in the cheap apartment area) after 18:00 (Mon-Fri, except Wed) and knock on the door. This event is randomized so it might take multiple tries before someone answers - just keep knocking on the door. If Diego opens the door, he won't let you in, cause he'll be jealous of you showing interest in Maria.

Once Eddy answers the door Vanessa will show up and reprimand Eddy for not paying his rent. Select:

"What a surprise!"
Then select one of the 3 red options (feet, breast or ass) depending on your preference - you need Vanessa and Eddy to catch you ogling her which will result in a fight with Eddy
Beat his ass

After the fight Vanessa will be upset with both of you and your Relationship with her will drop, but you'll progress to her next stage.

Stage 2: MILF chaser

Get a bottle of whiskey from Martha's store. You need to have 60+ Relationship with Vanessa and 80+ Handsome stat to succeed with this quest.

Go to the beach on Wednesday after 11:00, talk to Vanessa and select:

"Hi..." > Give her... > A box of chocolates
"I have a great whiskey for such a gorgeous lady! You're missing out on a lot!"

She'll ask you to make peace with Eddy and the scene will end there.

Stage 3: Making peace

You'll need ~$1000 to buy drugs for Eddy.

Right after you complete Vanessa's S2, go to Eddy's place (a hidden marker near the motorcycles in the cheap apartment area) and knock on the door. This event is randomized so it might take multiple tries before someone answers (it also won't work if Diego answers the door). When Eddy opens the door, select:

"Listen Ed... I wanted to talk...(Apologize)" > "I'll get you x doses..."

He'll try to antagonize you first, but eventually he'll ask you to bring him x amount of drug doses (up to 20), keep note of the amount. Go find and talk to Arnold. After he gives you the info, go and buy the amount of doses Eddy asked you to (💾 save before you start moving around, since there's a high chance you'll get busted by the police).

Once you got the goods, return to Eddy's apartment and when he opens the door, pick:

"I brought what you asked for...(about Vanessa)"

Stage 4: Boob alert

Get 2 bottles of whiskey from Martha's store. You need to have 85+ Relationship with Vanessa and 85+ Handsome stat to succeed with this quest.

Go to the beach on Wednesday after 11:00, talk to Vanessa and select:

"Hi..." > "I have a great whiskey for such a gorgeous lady! You're missing out on a lot!"

This will start a "happy drinking" mini-game (💾 save here), the goal is to get her drunk & happy stats to ~80+ (make sure her drunk stat doesn't reach 100 or the hang out will be over). Pick:

"Let's drink Vanessa!" ~x5
Give... > A box of chocolates
Talk about... > Work...
Compliment her... > "You have incredible breasts!"

Once she lays on her back, select:

Talk about... > "Your huge breasts are simply divine Vanessa..." (💾 save and re-load to see 3 variations of the following scene)

Stage 5: Wooing the MILF

You need to have 85+ Relationship with Vanessa and 85+ Handsome stat to succeed with this quest.

"Maybe we can have dinner together sometime?"

You need to own a car and have ~$2500 to pay for the drinks at the restaurant.

On Saturday evening after 20:00, go to Eddy's place and knock on the door. This event is randomized so it might take multiple tries before someone answers - just keep knocking on the door until Vanessa answers. Select:

You can choose to ogle her depending on your preference, if she catches you, apologize and it will increase your Relationship with her
"You look awesome (continue)!"
"We're almost there! (continue)"

Once you arrive at the restaurant a "happy drinking" mini-game will start (💾 save here), the goal is to get her drunk & happy stats to ~85+ (make sure her drunk stat doesn't reach 100 or the evening will be over). Pick:

Order expensive champagne! ~x5 (you'll need to repeat this a few more times later to get the stats for the blowjob scene)
Give... > A box of chocolates
Talk about... > Work...
Compliment her... > Use all 3 options
Talk about... > Personal question > About oral sex... (needs 65+ drunk & happy)
Talk about... > "Red lipstick suits you very well, Vanessa..." (needs 85+ drunk & happy) (💾 save and re-load to see 3 variations of the following scene)
Pay for everything yourself

After you return from your date and she's standing in the doorway, select:

"Turn around, please!" > Look at her ass! - you need her to catch you, repeat until she does
Reply: "I would fuck your butthole fatass bitch!" (📷 unlocks Vanessa bonus 2) (💾 save and re-load to see 3 variations of the following scene) - she'll only tease you, it won't lead to anything else at this point

Extra 1: cafe double team

You need to complete Bella's S3 and Nestor's S0 first and make peace with Hector, to be able to invite Nestor to the cafe. Additionally, you need to have 85+ Relationship with Vanessa and 85+ Handsome stat to succeed with this quest.
You'll also need ~$3500 to pay for the drinks at the cafe.

After you and Nestor have drinks at the cafe and Vanessa shows up (📷 unlocks Vanessa bonus 1), select:

"Excuse me, madam! Allow us to keep you company for the evening!"
"Hola, Vanessa!" > "Will you join us?"

This will start another "happy drinking" mini-game - the goal is to get her drunk & happy stats to ~95+ so that you can challenge her to a game of Hot Spot (Nestor's stats don't matter at this point, so focus solely on Vanessa, also, you don't need to worry about her drunk stat reaching 100). Pick:

"Let's drink!!!" ~x5
Talk to Vanessa > Work... + Eddy... + Diego... (needs 55+ drunk & happy)
Talk to Vanessa > Personal question... > Boyfriend... + About fetish... (needs 65+ drunk & happy) - add some drinking in between to keep the drunk stat up
Talk to Vanessa > "How about playing Hot Spot?" (needs 90+ drunk & happy)
Pick: "Let's play for money!" and beat her once
Repeat, this time pick: "Let's play for wishes!" > "I'm ready! Let's go Vanessa!" win the game
Talk to Vanessa > Personal question... > About oral sex... (needs 65+ drunk & happy)
Talk to Vanessa > Personal question... > About vaginal sex... (needs 75+ drunk & happy)
Talk to Vanessa > "How about playing Hot Spot?" > "Let's play for wishes!" > "Agree!" win the game to have a threesome scene with her (💾 save and re-load to see 3 variations of the following scene) (📷 unlocks Vanessa bonus 3)
Pay for everything yourself - you can also choose to split the bill with Nestor and Vanessa (but you won't get bonus Relationship points with Vanessa)