Have a lovely holiday. We'll return Friday. If you're feeling a feeling and have a question about relationships in your life, end the year by asking it.
Former letter writers can send an update about their lives to firstname.lastname@example.org with "update" in the subject line.
I have been in an on-and-off casual relationship for years with the same guy. I met "Guy" when I was 23. At the time, I was divorcing my first love and had a toddler. Guy was in his 30s and focusing on his career while dating as many different women as he could. We would go clubbing together. He was my wingman and vice versa. We always had the best time – and still do.
In my latter 20s, I found myself in a serious relationship, but when it ended I was right back to where I was before – with Guy. By the time I was 30, all my friends were getting married and I wanted to do the same. But a friends-with-benefits relationship can't last forever, right? Guy had no desire to marry or have kids.
I met someone else, got married, and kept my distance from Guy but thought about him often. He was busy with a younger woman. Then, after experiencing a natural disaster with my husband and clearly seeing that we were not a good team, I divorced him. I resumed hanging out with Guy when the divorce was finalized, which was well over a year ago now.
My child is older now, so I have more time. Guy has dated a more women with no intention of having children. We've experienced great times, a fun vacation, and sad times due to family illnesses and deaths. I don't want to risk losing our trust, respect, and special bond to demand something more serious. Am I in a secret open relationship or still friends-with-benefits? Am I settling? Does it matter? He feels like home and family to me.
Also, do I pursue other relationships? Would they even be successful as long as he is in the picture? This time I know I am not willing to take him out of it. He is my best friend now, and I am his.
– Almost 40
You don't have to make any demands. Instead, why don't you ask Guy how he defines the relationship to himself and others? "Best friends" should be able to talk about feelings. You can ask the simple question: "What are we doing?"
The answer might be that you are, in fact, in a secret open relationship as friends-with-benefits. It sounds like he likes it like this – having a fun, intimate relationship that involves support, closeness, and consistency without any kind of on-the-record partnership. That kind of relationship can be great if it's what you want, too.
But honestly, if you're longing for the kind of boyfriend who can show up and introduce himself as, well, your boyfriend, you should be with someone who can deliver. A great almost-relationship isn't so wonderful if there's a feeling in the pit of your stomach telling you it isn't enough.
Talk to Guy. Be prepared to tell him what you want because that's part of the conversation. Also think about what you don't know – because maybe you can define things together.
Be as honest as possible, even if it feels risky. That's the best way to figure out if you should be seeking out others.
Readers? What would you ask Guy?