It really shouldn't have surprised Santiago when he saw you at Benny's housewarming party. It made sense, you were Frankie's sister and Benny's friend before you were...well, his. And now, you weren't. He couldn't count the amount of times he'd used Frankie or Will's shoulder to cry on over you, because truth be told, the break up was one of the things that had hit him hard in life, even after all he had seen and done, losing you was still something that rattled him.
Hours had passed into the party, and you both knew you were looking at each other from across the room. Stealing glances every so often, never holding eye contact. The break up hadn't been anything hard or dramatic it just...didn't workout. What could you do then?
Finally, he decided to approach you when he saw you getting a drink, holding his own beer in his hand as he sort of awkwardly came up to your side, passing you a polite smile.
"Hey..." he greeted softly, giving you a slight once-over "it's been a minute. You look nice"