Philip von Hahn, a 30-year-old tech investor on the Upper East Side, attended a holiday party on Sunday night to take his mind off the recent dissolution of his three-year relationship.

“We’ve been weighing it for the past few months,” Mr. von Hahn said of the decision to end things. The holidays, however, added a sense of urgency, as he and his ex-girlfriend weren’t able to agree on who would visit whose family for Christmas, or if they even wanted to spend this time of year with each other again.

Although fall and winter have affectionately become known as “cuffing season” in recent years — a period where couples stay indoors, cuffed together throughout the cold months — they can also be a fraught time that puts pressures on newer relationships.

A small infraction like not buying a thoughtful Christmas gift or being reluctant to visit your partner’s family for the holidays can be the excuse a hesitant partner was looking for to call it quits. Ghosting feels like an easy option when people can use their travel plans as an excuse to be absent, and time apart can make staying connected difficult, especially if a relationship is already on shaky ground.

Mr. von Hahn said that he and his ex-girlfriend both decided to break up after realizing the relationship wasn’t progressing to the next step (“Like, get married”). He said he felt good about the decision, despite still needing time to adjust, and was crashing with a friend in Brooklyn after moving out of the apartment they shared.

For Christmas, he planned to return home to Toronto to spend time with his family “and convalesce.” He was looking forward to having a busy holiday schedule to keep him occupied.

The end of the year is also often a time of reflection and a yearning for a “new year, new me” that can be at times one-sided.

Beth Booker, a 33-year-old public relations specialist in Naples, Fla., had met her ex-boyfriend in September on Bumble and hard launched as a couple in November. He broke up with her this past weekend.

“It really sucks when you finally decide to take that leap and you feel safe enough to do it, and they can’t catch you,” she said in a phone interview on Monday.

He returned home to Pennsylvania around late fall, and, after agreeing to try to make a long-distance relationship work, he had a change of heart during a conversation about their plans for the new year.

Despite films on the Hallmark and Lifetime channels that would like to convince people that the holidays are the most romantic time of the year, they can feel especially lonely if you’re single.

Tejah Larkin, 31, describes this time of year as the moment many couples choose to make things official, so holiday parties and ugly Christmas sweater gatherings can feel harder for people like her who are still casually dating.

“During this time, the events are not really gauged for the singles, because most people probably have been dating since the summer and now they’re trying to lock it down,” said Ms. Larkin, who lives in East Orange, N.J. “Most people are inside with their significant others.”

Ms. Larkin is currently seeing a man with whom she grew up after reconnecting in late October. It’s in the honeymoon phase, she said, and they are focused on building atop their old friendship and seeing where things go. He plans to return home to Georgia for Christmas and New Year’s Eve. She hopes they will stay in contact during that time.

“This will be the first time either of us have been not in the same area communicating, so hopefully we keep the same consistent communication,” Ms. Larkin said. “It’ll be a real test.”

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