Girlfriend #8 is Mila Munch. She invited him to hang out at the Bluffs. As soon as she agreed to to become his girlfriend, she ran away...to go swimming. https://i.imgur.com/XqduZ7I.png
Then she invited him on a date there, and again wanted to go for a swim. He sent a flirty text to Ulrike, trying to make up. She invited him out for drinks, and promptly ditched him. Then Myra Anand invited him to the Romance festival, which is probably actually not the best place to pick someone up, when you have multiple girlfriends who might be there A trip to the Blue Velvet nightclub gained a few new possibilities, but a bunch of awkward encounters, since Candy Behr was there keeping an eye on him.
Girlfriend #9 is Aya Seddiki, here at the park in Willow Creek, which is one of his favorite dating spots. So he has to be careful about which Aya he is talking about. Or to. He asked her on a date, which was probably a mistake. Although he has enough charisma by now that he could get her in a very flirty mood, he was too hungry and tired to be in the mood himself, and had to settle for a silver instead of a gold level date. The teenager who was watching and wanted to join in wasn't much help, either.
https://i.imgur.com/C4v98cb.png
He needs to kiss two more Sims to qualify as a Romance Juggler.