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Guy Conflicted After Getting His New Girlfriend Pregnant Only To Find Out She’s His Sister’s Ex

Is there an unwritten rule in dating about best friends and family? You know, don’t tread where they’ve been?

And yet, there are stories of widowers who marry their late brother’s widow or vice versa that lead to happiness. Or divorced people who end up with a sibling’s ex and find bliss together.

Is this taboo?

Reddit user ThrowRAway636—a 27-year-old man—explained his situation with his 23-year-old sister and her 25-year-old ex to the “Relationship Advice” subReddit for, well, advice on one of these situations.

The original poster (OP) explained:

“Don’t know how to tell my sister  her ex and I are gonna have a baby.”

His story goes:

“I want to be happy about this because I’m going to be a dad for the first time but also feel awful and don’t know how this is going to affect my sister, Mel.”

“She’s my half-sister, same mom but different dads, so our last names are different and we don’t look alike much.”

“Plus I was studying abroad when my sister came out as a lesbian 3yrs ago.”

“This is how Jenna (my girlfriend—her ex) and I never connected the dots until after we were seeing each other awhile.”

“Mel developed feelings for Jenna when they were coworkers and they started going out. She was basically the person who helped my sister realize she was attracted to women and came out of the closet.”

“I never met Jenna when my sister was dating her and only saw a picture of her once but that was when Jenna dyed her hair blonde.”

“We were both busy with our lives so we didn’t communicate much.”

“I found out they broke up and Mel was completely heartbroken. She said Jenna no longer had feelings for her and was having doubts about her sexuality so she decided to end their year long relationship.”

“I ended up moving back months after their break up after I graduated and found a new job.”

“I eventually decided to try dating again.”

“Went on a few Tinder dates and guess who I got matched with? Yeah, Jenna.”

“But like an idiot I didn’t think anything of it. I mean there’s like a million Jenna’s out in the world.”

“We had our date and really clicked. She’s so sweet, funny and genuine.”

“I knew by the end of the date I was gonna fall for her hard.”

“And we did. We loved spending time together and things got serious pretty fast.”

“[The pandemic] made it hard to see each other often but we basically FaceTimed several times a day so we were still close in a way.”

“Barely 2 months ago we finally figured it out. She slept over at my place and I got a call from my sister telling me how my mom’s doing (one of her coworkers got [the virus] so my mom got tested; came back negative).”

“We talked about my family, I showed her a pic of my sister and she froze. Like literally her face went white.”

“I asked her what was up and that’s when the whole thing came out.”

“We were both pretty shocked. Jenna knew Mel had a brother but because I wasn’t in much contact with my sister back then we just both never knew.”

“It was awkward but we both had (still do) deep feelings for each other and well…kept going out.”

“I haven’t been able to figure out how to tell my sister and now we’ve just learned Jenna is pregnant.”

“Which we’re both really excited about by the way. It wasn’t expected and this relationship has only been going on 11 months, but we’re still looking forward to being parents and love each other deeply.”

“We’re making plans to find a bigger place to move in together before the baby gets here.”

“I just have no idea how I’m going to tell my sister all this.”

“She was really broken when they split up and as far as I’m aware hasn’t dated since. Jenna was pretty much her first love and I’m scared this is going to crush her.”

“She’s basically going to be the aunt of her ex’s child and I’m not sure what’s the best way I can break the news to her.”

“Anyone have any advice on how to proceed?”

Plenty of feedback was provided, though most focused on things that already happened and can’t be changed instead of advice for the future.

“Advice number 1- tell her ASAP. Tell her this exact story.”

“Advice number 2- prepare yourself for the worst outcome because it may happen. Your sister might never want to see you or Jenna ever again.” – freelanceredditor

“You should have told her 2 months ago when you figured it out. By waiting, it looks like you were intentionally keeping her in the dark.”

“Tell her the truth and that you both only recently figured out the connection.”

“Honestly, though, it’s very likely she’s going to cut you out of her life at least for a while.”

“Knowing you and Jenna are together and having a baby will hurt badly enough; actually having to see you together and see the baby will probably be more than she can handle.”

“Not trying to make you feel like you shouldn’t be with Jenna, just want you to be prepared and braced for the loss.” – the_last_basselope

“You have to tell her and you have to be prepared for the worst. You have at this time dated your girlfriend less than how long she and your sister dated.”

“Plus she’s not only your sisters ex, she’s your sisters first love. That’s going to hurt her maybe for forever.”

“You have to accept that by choosing your girlfriend you may likely lose any relationship with your sister. And keep in mind this is likely going to cause a huge rift in your entire family.”

“But you still have to tell her. You should have told her 2 months ago when you figured it out. It was unintentional until two months ago, anything after that is lying by omission.” – jupitersreject

“You prioritized your relationship with Jenna over your relationship with your sibling the moment you found out and didn’t tell her. Then, you made the choice to not tell her every day for 60+ days following.”

“I won’t even touch on the issue/concerns anyone would have over beginning a family with a relative stranger after only dating 11 months & admittedly doing most of said dating over the phone.”

“Regardless, you’re a crappy sibling for knowing and refusing to tell your sister. It was selfish of you to keep this from her.” – waIrusgumbo

Others questioned OP’s actions before asking for advice.

“I don’t know, to me moving in and having a baby with someone you’ve known for less than a year who happens to be your sister’s ex is uh…..really bad news.”

“I don’t think you’re as innocent here as you’re making yourself out to be.”

“You chose to have a baby with this woman and thus permanently involve her in your life before even telling your sister that you two were dating. Mel should cut you out of her life in my opinion.” – phanaerothyme

The OP responded to some of the criticism.

“I never said I was innocent. I’m here asking for advice on how to deal with the situation.”

“We didn’t plant to have a baby but are looking forward to it and making the necessary preparations.”

However most people remained focused on the pregnancy instead of providing usable advice.

“I can’t understand having a kid with someone you’ve never lived with and don’t know well enough that their dating and work history never came up to the point where you have zero idea they dated your sister….(don’t know how it’s possible to not know, I don’t buy it) like if that was shocking news instead of just basic background info do you even know one another enough to live together let alone parent a child?” – hedaleksa

OP did get a few pieces of usable advice.

“Wow, so many people focused on everything but the actual request.”

“OP didn’t ask for comments on whether pregnancy is a good idea or what should have happened in the past. Ship’s sailed folks, so unless all y’all have time machines, stop wasting people’s time with useless comments.”

“OP, I suggest tell her first and then immediately tell the rest of your family. Do it all in writing in addition to on a call (if it goes as badly as you think, you’re probably not going to get a chance to tell the whole story, especially to your sister).”

“Be honest!”

“‘I met a wonderful woman, we clicked right off, fell in love, then on (give the specific date) we both discovered she was Mel’s ex. Since then we’ve wrestled with how to tell you without hurting you’.”

“‘Not knowing how, we waited too long to tell you. We’re sorry for taking so long’.”

“‘But we won’t be ending our relationship. We’re pregnant and intend to start a family together’.”

“That’s really all you can do. Rip off the band-aid and be prepared for backlash.”

“You may find yourselves ostracized by your whole family.” ~ LakotaGrl

The consensus is OP should have told Mel as soon as he found out. There’s little he can do to minimize the damage at this point.

He’s going to have to tell her and hope things will work out in time. Maybe it will turn out better than Redditors predicted, but he’ll have to wait and see.

Written by Ben Acosta

Ben Acosta is an Arizona-based fiction author and freelance writer. In his free time, he critiques media and acts in local stage productions.