Sometime after Halloween – and through New Year’s – a lot of people start asking big questions about their relationships ... or lack thereof.
Like, “Do I like the person I’m dating enough to buy them a Christmas present?” Or, “What is happening to my friendships as some of us couple up?” Or, “How can I smile through another single New Year’s Eve?”
(For the record, I think New Year’s Eve is a very great night to be with friends and family, as opposed to a partner. Especially the wrong partner.)
Sometimes people spend their fourth quarter setting intentions for the next year. Maybe they wonder whether marriage is on the table. Or divorce. Or something in between.
What’s your relationship question as you approach the holidays? Ask it here.
In the meantime, here are seven of my favorite holiday Love letters entries letters from years past.
This letter was from someone thinking about an ex during the holidays. They said, “There’s just this huge amount of hurt that I haven’t been able to get rid of. And the uncertainty of knowing if we’ll ever even talk to each other again makes it hard for me to move on properly.Am I being unreasonable?” They signed their letter “Home Alone” ... which is a very holiday-times thing to do.
Two years ago, someone wrote to me about sharing a bunch of friends having the same crush. Who would win this woman’s attention? The letter writer? Someone else? “Over Thanksgiving, she texted me saying she was thinking about me. I’ve invited her to things since and we seemed to be connecting more.” I wonder what happened to this group.
Just before Christmas in 2018, a letter writer told me they’d met someone nice. Someone with promise. Except … he wasn’t ready. “He apologized several times for misleading me. He said he simply wanted a hookup. Likely in an attempt to heal his broken heart and fill that void.” Timing isn’t everything, but it’s important. I’m so glad this relationship didn’t last through New Year’s.
The end of the year means new beginnings for a lot of students. In this letter, a writer asks how a relationship will survive an upcoming semester of long-distance. “I’m so worried about leaving him for a few months that I don’t even feel excited to go abroad anymore. Is this actually a situation I need to be worried about? How do I keep us both happy while we’re so far apart?”
December of 2020 was a complicated time. Vaccinations were on the horizon. Many people were still in lockdown, avoiding family holidays until it felt safe. For those who went through quarantines together, there were big questions. Like, “Now what?” Were relationships formed in a bubble meant to last? Here’s one of those letters.
In 2009 (yes, we turn 15 next in 2024), a person wrote in to say they didn’t like their new girlfriend’s friends. “Most of her guy friends are the simple, meat-headed type you’d expect to see in a Coors Light ad. Funny topics consist of inside jokes from their high school days or making fun of other people in the room. Not exactly my top two interests. Most of her girlfriends are the type who want to date the aforementioned guys. Their lack of personality reminds me of Stepford Wives but without the class or grace.” Yikes. My assumption is that almost 15 years later they are not together. But who knows?!
Speaking of “who knows” …. sometimes we do get to know. Really, some of my favorite holiday letters are actually letter writer updates, which I try to run at the end of the year. Here’s an example of one set of updates from a few years ago
Also, an official call to former letter writers: Please tell us what happened after you wrote in. Are you all good? Have a new problem?
You can send a question – or an update – through our anonymous form. New letter writers: I’m here for you too. I’ll be spending some of my holidays doing what I love most: checking my inbox and reading.