Lena Kaligaris

   Lena Kaligaris, or also known as "Lenny", is a shy, introspective aspiring artist of Greek heritage. Lena is very beautiful but shies away from others because she always worries they only like her for her beauty.

Early Life
Throughout the books, Lena tries to hide and downplay her beauty so that others don't judge her for it. Lena considers her biggest weaknesses are her inability to love and trust freely and her tendency to avoid the real situation because it is emotionally difficult to deal with.

She feels especially guilty that people like her on-again-off-again boyfriend, Kostos, and best friend, Bee, who have lost so much in their lives, can live and love freely when she is reluctant to trust others.

Her friend, Tibby, adds that "If you asked Lena to pick A or B, she'd always choose C," meaning that Lena has difficulty following her emotions.

Rather, she justifies and overthinks everything. Aside from Girls in Pants: The Third Summer of the Sisterhood, Lena's storylines in the books always seem to come back to Kostos, her first love.

Appearance
She is very beautiful. She has long dark hair that is almost always pulled back in a ponytail or messy knot and "celery-green" eyes.Her friend describes it as deep emerald pools.

In the movie she has blue eyes. She likes to dress in something that doesn't show she actually has a shape. Later when she meets Kostos she starts wearing more revealing clothes.

Romantic relationships and relationship with Kostos Dounas
Lena first meets Kostos in the first summer of the Sisterhood while vacationing in Greece with her grandparents. Though she is reluctant to act on her emotions at first, she eventually gives in to her feelings, a momentous event for her.

Prior to the events in The Second Summer of the Sisterhood, Lena and Kostos exchanged letters and kept up a long-distance romance, but her fear of separation anxiety caused her to cut the relationship off.

Unbeknownst to her, Kostos proceeded to have a rebound affair with Maria, a local woman. In the summer, he visited Lena and they reconciled, coming close to making love, but stopping just short. He returned to Greece unannounced, leaving Lena hurt and confused.

Several weeks later while in Greece to attend her Bapi's funeral, she met with Kostos who introduced her to Maria, who had told him that she was pregnant. In an effort to be an honourable man, Kostos hastily married Maria.

Heartbroken, Lena returned to America. She seemed briefly interested in Carmen's stepbrother, Paul Rodman, but the interest remained only an interest.

In Girls in Pants, Lena has learned that Kostos's wife had never had her baby, but was unsure of why. At that point, Lena has not considered dating anyone new.

In Forever in Blue, following Lena's first year away at school, Lena has a small romantic fling with student painter Leo. Kostos encounters Lena briefly in her dorm room to elaborate on what had happened with Maria; she had lied about being pregnant to trick him into marrying her and they had since been estranged.

Angry at him for abandoning her, Lena sends Kostos away. She has a relationship with Leo but soon breaks it off before it goes further. When Effie's thievery and eventual loss of the Pants leads the girls to Greece, she meets with Kostos, who reveals that he had planned to propose to her when he met with her in Rhode Island. The two forgive one another and contemplate if they will ever be able to love anyone else, but do not rekindle their romance. Kostos whispers in her ear "Someday" in Greek before they part ways.

In Sisterhood Everlasting, Lena, now twenty-nine, has been dating humble sandwich maker Drew, and though she doesn't see the relationship going anywhere she does not seem to mind.

They lose contact following Tibby's death, and while in Greece Lena spends several long, emotional nights with Kostos reminiscing and discussing life. Kostos, now a successful banker living in England, still cares deeply for Lena, though they do not experience any romance while in Greece.

Upon her return to Rhode Island, after a period of grieving, Lena finally opens Tibby's letter, which leads her to a farm in Pennsylvania along with Kostos. The two finally realize that they were meant to be together and the novel leaves off with them together.

Art, education and career
Lena's talent for art and sketching is apparent from the first novel, and she bonds with Kostos through sketching him. She often has a difficult time drawing faces in her younger years because of her shyness and inability to connect with people. However, she has many experiences in the early books in which she bonds with people through drawing their real selves underneath their armour, including Paul Rodman, her sister Effie, her grandmother Valia and her stern father.

Despite her father's opposition because of the impracticality and the often-times racy subject matter, he agrees to let her attend art school at Rhode Island School of Design. She is recognized as a gifted artist but often fails to stand out because of her shyness. During her first summer at RISD, she takes an extra course where she meets Leo and becomes flustered at the idea of painting him in the nude. However, he helps her loosen up slightly as she lets go of some of her discomfort around him.

Following her graduation, Lena went on to attend graduate school, resumably also at RISD, and was apparently the first master's graduate to be given a salaried teaching position at the school straight out of graduating. She also makes some money off of selling her own art.