Owing to the preponderance of foot traffic weaving in and out of the courtyard and the confoundingly asymmetrical layout of the courtyard itself, it was perhaps no surprise that Monte Steinhouse, a med student interning at a nearby surgical center, always seemed to appear out of nowhere. A thin wisp of a man, he had a tendency to disappear into a crowd, which made it difficult for Calisto to ever feel prepared for his sudden appearnces. He had made her acquaintance through his co-worker/erstwhile drinking buddy Eric Arnold, who was Naomi's fiancee. This introduction had led to the realization that the two of them worked in adjacent buildings. In truth, Calisto had always noticed the guy slinking around the square, and it had struck her as strange to see the man scrubs constantly smoking cigarettes by the street corner. She would have assumed that people in the healthcare industry, as a rule, live healthy lifestyles. It reminded her of vintage cigarette ads from the 1950s showing testimonials from doctors promising that this particular brand of cigarette was more beneficial to your health than any other.
Calisto couldn't say much though, since she was a prodigious smoker herself, a habit which had been exacerbated by her mother's death 6 months ago. "With Mom gone, no one is around to tell me to stop anymore," she reasoned. What was odd was that she and Monte had never shared a smoke together, until that night when Naomi and Eric introduced them. It was only legal to smoke in a handful of isolated areas of the Square, which meant that one was sure to see the same faces puffing away in their little nooks and street corners, with a rotating cast of new additions, day in and day out, often clockwork in their timing. So their paths had surely crossed any number of times during the year-and-a-half in which Calisto had been working there. In fact, her inward reaction when being introduced by her roommate had been "Oh, it's this guy." Certainly at the time she'd had no reason to believe that Monte would soon be owing her a great deal of money.
The truth was, guys like Monte had always given her the douche chills. There are certain types of people in this world that just don't commingle with us, and for Calisto he was one of them, at first. It turned out they had a great deal in common once they bothered to find out. They both had recently suffered the loss of a parent and were rebounding from the dissolution of a long-term relationship, in part because of the fallout from that loss. In retrospect she would come to believe he had zeroed in on these signifiers of vulnerability to take advantage of her, or at least she told herself when things were going badly. But although they had been through similar tragedies, they responded to them differently. Monte seemed to take it in stride and convert his experience into instant wisdom (he'd say "people die everyday, I just happened to be a acquainted with this one," as if his dad were someone from high school who he only recently reconnected with on facebook), where Calisto would question the meaninglessness of a mother being taken from her just as they were reconnecting.
Calisto's mother, in fact, turned out to be the reason she gave the money she left her to Monte in the first place. She had owned a small boutique, really a kiosk that sold dresses, while Calisto was growing up and therefore never spent much time for her daughter. But then as soon as it was time to go away to college, her mother had sold the now-profitable business to a competitor, causing no small amount of resentment on her child's part. "Oh she's too busy for me right up until it's time for me to go away, is that it?" Calisto would think to herself. With no other recourse, she turned to harder partying and neglecting her responsibilities, which led to her losing her scholarship and dropping out of college altogether.
Still, even seeing her mother in the sickbed, dying from cancer years later, she could not forget how neglected that selling of Haughty Couture had made her feel. Her mother, after all, used to refer to her business as "my baby", and in all the years she could remember, Calisto had never been referred to this affectionately. As if sensing that she had not held up her end of up the parental bargain by prioritizing her entreprenurial venture over it, she left two dying requests to her only child, which she had raised alone (however distractedly).