I’ve known my best friend (36F) since we were in middle school. I’m also very close with her younger sister (34F), who I’d also consider one of my best friends. We were so close that the three of us lived together in college and again after college while in grad school. They’re basically a second family.
Their brother (25M) is the baby of the family, and I’ve obviously known him for a very long time too.
For context, I was in a longterm relationship that turned pretty bad. I stayed much longer than I should.. I wanted a partner who was social and excited about trying new things, and my ex just wasn’t. After we broke up, I felt pretty isolated. I felt like I had to go and do and make up for lost time. Most of my friends are married or focused on their families now, which made that period feel especially lonely.
Around that time, their brother and I started spending time together. At first, it was completely platonic. We’re both single, very social, and love trying new things. It felt good to have someone who actually wanted to do things with me again. There had always been a playful, flirty dynamic between us, but I didn’t take it seriously. It’s just part of his personality and he’s like that with a lot of people. At one point, his sisters jokingly told me I was “never allowed” to date him, which we all laughed off at the time.
Those “just friends” outings gradually became something more. It wasn’t planned or dramatic, but it just happened. We kept it casual and private, with no labels, promises, or longterm plans. I honestly thought we had it under control, but apparently we didn’t because I recently found out I’m pregnant.
I want to explain why I decided to keep the baby. I’m a single woman, but I’m financially stable, have a solid career, and can fully support myself and a child. The father knows and is fully involved. We’re not pretending this is simple or romanticized, but we’re both committed to being responsible and prioritizing the baby. I’m 36 years old, and while I know it’s often very possible to have children later, how long would it take for me to find the right man to do it with, get married, do everything the “traditional” way? While I’m overwhelming anxious about it, I feel like this is the right decision for me at the end of the day.
If this had been some random guy I didn’t feel I knew or could trust, I almost certainly would not have continued the pregnancy. My choice is grounded in the fact that I know him, I trust him, and we’ve thought through how to handle this responsibly.
Where I need advice is telling my best friend and her sister, and the rest of their family for that matter. Their parents have treated me like another daughter. You’d think that’s mean they’d be happy about this, but I’m so nervous they’ll feel the opposite. This is their baby, their only son, and I’m sure this isn’t what they have in mind for him.
I know my best friends will likely to be upset that I’ve waited close to a year to tell them about any of this. When does it cross over to innocently keeping something private and discreet o outright lying to somebody? I also anticipate that they may raise concerns that their brother is too immature or irresponsible, which has been a recurring theme in their family. I get that they still see him as their baby brother, but I also genuinely believe he’s capable of more than they realize.
I want to handle this honestly and respectfully, while making it clear that we’ve thought this through and are committed to taking responsibility for the baby.
I’m looking for advice how to tell them in a way that acknowledges their concerns without turning it into judgment or argument. How do I not get overly offended or defensive when they most likely express their honest opinions? How do I navigate their opinions while maintaining my relationship with the family? I don’t want to come between him and his family and I can’t afford to lose my 2 best friends.
I really want to handle this as thoughtfully as possible.
TLDR: I’ve been in a casual relationship with my best friends’ brother for close to a year, which we’ve kept private. I’m pregnant and we’ve decided to keep the baby. I fear this will cause some strong reactions and opinions from his family members, and I’d prefer to not ruin any relationships over this. How son navigate everything as thoughtfully as possible, while still remaining firm in my decision?