Love Life: I Fell for Her Despite Her Fling With My Sister

Love Life* is a Zikoko weekly series about love, relationships, situationships, entanglements and everything in between**.*

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Jessy* (29) and Lauretta* (27) met in 2024 when she attended his family’s barbecue event.

On this week’s Love Life, they talk about falling for each other despite Lauretta’s history with his sister, the awkwardness of announcing their relationship, and how that unresolved tension still hangs over their love.

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What’s your earliest memory of each other?

Jessy: It was Boxing Day 2024, at a barbecue at my family’s home. My sister, who’s just a year and seven months older, had begged me to go to the estate gate because the security guards weren’t letting her friend in. I grumbled about it because it’s a long walk, and I’ve always hated the idea of running errands for her. But I went anyway since she wouldn’t let it go and was actually occupied with another task.

When I got to the gate, the friend in question turned out to be Lauretta. I already knew a few of my sister’s friends, and they were usually tomboys, so Lauretta stood out to me immediately. My first thought was just, “oh, she’s pretty.” She also wore a flowery gown that made her look like a fairytale princess.

Lauretta: I was actually hesitant when Jessy showed up. I’d been so frustrated with the security guys that I didn’t realise his sister had left me messages on WhatsApp saying someone else was coming to get me. I just saw him talking to security at the gate, and when he walked up to me, I thanked him and then asked, “Sorry, who are you?” I didn’t mean to be rude about it, but I genuinely didn’t know who this stranger was.

Jessy: That question felt like a small stab in my ribs, but I played it cool and just introduced myself.

Right. Was it a quiet walk back to the house?

Jessy: I actually tried to make conversation. I asked a few questions to break the ice, but she was giving me pretty flat, one-word responses the whole time. I assumed from that alone that she wasn’t feeling me at all.

Lauretta: Honestly, I was already super stressed from the whole gate situation and the long walk in the heat. I was also lowkey angry at his sister. It was the first time I was visiting her house, and it felt weird that she couldn’t even make the time to come pick me up. Everything Jessy was saying was passing through one ear and out the other. I just wanted to sit somewhere cool and relax; it genuinely had nothing to do with him specifically.

Jessy: When we got to our block, I handed her off to my sister pretty quickly and didn’t really stick around to talk further. We didn’t actually see each other again until March the following year, several months later.

Oh. Did you think about her at all during that gap?

Jessy: I asked my sister about her once or twice in passing, but never really got a clear or definite answer from her. I just assumed Lauretta was one of my sister’s flings and left it at that in my head.

Lauretta: Funny enough, I actually thought about him quite a lot, even though I’ve never really told him until now. He did look good on that first day. I remember seeing his nose ring and beard and just thinking he’s cool. But I also felt bad about our little interaction that day. I was hoping to apologise to Jessy before I left their Boxing Day party, but I didn’t see him. I always told his sister to extend my greetings. I’m not sure if she ever did.

Jessy: Nope. Not a word from her.

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Screaming. Let’s talk about the reunion in March. How did that happen?

Lauretta: I was supposed to go out with Jessy’s sister, and the same gate issue came up again, except this time, she wasn’t picking up her calls at all. That’s when I remembered she’d shared Jessy’s number with me the last time this happened, so I called him instead as a last resort.

Jessy: I recognised her voice the moment she said hello, before she’d even properly introduced herself. She explained she was stuck at the gate again, and I mentioned my sister was in the shower and couldn’t come. I wasn’t exactly inspired to walk all the way out there again myself, since she hadn’t been very chatty with me the first time around, so I just called the gate and told them to let her through.

Right.

Lauretta: I ended up calling him back because I genuinely didn’t remember the way to their house from the gate. So he had to come get me anyway, whether he wanted to or not.

Jessy: She looked just as pretty as the first time, maybe more so, and I remember thinking I could actually see myself dating her. But because of the last experience, I already had my guard up, so I wasn’t really pushing for a conversation. I think I was a few steps ahead of her. Then, she started talking about the flowers or the road, I can’t even remember. Either way, she was a completely different person from our last encounter. She was chatty, thanked me properly for walking out, and she even asked why she hadn’t seen me around for the rest of the party back in December. She said she had planned to apologise. And those words just melted whatever hard feelings I had. We just talked about random, easy things on the walk back, and that was that.

So what happened next?

Lauretta: I sent him a thank-you message on WhatsApp later that day, nothing deep, just manners. But that’s really what started our friendship.

Jessy: From there, we’d both react to each other’s posts, check in just to chat and nothing beyond that. The energy felt really reciprocated, too. I didn’t at any point feel like I was pushing, and I don’t think she felt the same way. The whole time, though, I never actually asked her or my sister directly what was going on between them.

Why?

Jessy: I guess I just wanted to do a bit of quiet investigating on my own, instead of asking directly. My sister can be quite nosy and suspicious. If I’d asked anything about Lauretta, she would have wanted to know why I was asking. And she wouldn’t stop until she found out. And I guess I didn’t want to ask Lauretta, just so I wasn’t in her business or sending any signal.

Eventually, though, I asked my sister instead. She said they were just having fun; nothing serious between them. As expected, she asked why I even wanted to know, and I played it off like idle curiosity. She had no idea by that point that I’d actually gotten close to Lauretta myself.

Lauretta: His sister told me, actually. But I waved it off. I think it was somewhat hard to place what Jessy really wanted. As far as I knew, our relationship was purely platonic. He didn’t give any signals that he was into me. And I’m not one to make first moves. I prefer when a partner moves to me.

I also didn’t think he’d see me in that light since he already knew me with his sister. I felt he would have put a few things together and figured out what we were up to. So we were really just in a casual friendship.

Got it. How long did this last?

Jessy: About three months. As she said, we never really pushed the conversation forward for our different reasons. However, after a while, I noticed Lauretta had stopped visiting my sister as often. Around August, I texted her just to catch up, since we hadn’t spoken in a long while. It was our regular banter, but deep down, I was a man on a mission.

I can’t remember if it’s the same day that I texted her or days later, but during one of our conversations, I stylishly asked if she’d dumped my sister. Then she went, “Dump as how, we’re just cool, we had our fun and we’re cool.”

I took that to mean nothing serious was really going on between them. During one of our earliest conversations, too, Lauretta had mentioned that she was bisexual. I guess that was why she was always somewhere in my head.

I’m guessing you made your move now that your sister was somewhat out of the picture?

Jessy: In a way. I invited her to a party that same week, nothing planned beyond just wanting her there. She came, we had a good time, and that’s the night I ended up confessing my feelings, though I was admittedly slightly high at the time, so my inhibitions were a bit lower than usual.

Lauretta: I actually didn’t want to go to that party at all. I could sense where things were headed even before he said anything outright, and some part of me wanted to avoid that conversation. I should also clarify something here; what happened with his sister was really just us making out once, and that was the full extent of it. She prefers studs, and I’m not one, so in my own head, nothing had really happened between us in any serious sense. That’s partly why I felt comfortable answering Jessy’s call in the first place without overthinking it.

When he started talking about his feelings and how we could be a thing, I told him plainly that he was drunk and that he should come talk to me again properly when he wasn’t. I didn’t want to take anything said in that state too seriously, even though I knew he meant it.

Curious, Jessy. What do you remember about that night?

Jessy: Honestly, I couldn’t remember half of what I’d actually said; it’s all a bit of a blur looking back. Two days later, I worked up the nerve to text her and ask, “Did I ask you out at the party?” She confirmed it had happened, and I was like, “Oh, shit!” Then I begged her to walk me through everything that went down that night. She told me about us dancing together for most of the night, and how things eventually built up to me asking her to be with me.

Lauretta: Then, after I finished narrating how the night played out, he told me he meant everything he had said. Then he asked me out again, properly this time. Although I still told him he needed to take me on an actual date first before I’d give him an answer.

He planned the date, and we became official on September 10th, 2025.

Nice. But you both didn’t see the need to inform Jessy’s sister first before you committed to a full relationship?

Lauretta: Personally, I didn’t see the need. Whatever happened with his sister barely registered. I don’t feel comfortable getting into details, but even the one time we made out, we still had our clothes on. Although I flagged it to Jessy early on, we can’t ignore that I knew his sister first, and we could have actually been a thing if we’d worked it out.

By that point, though, she and I weren’t really talking much anymore anyway, so I personally didn’t feel an urgent need to reach out and explain myself to her. But I did tell Jessy plainly that he needed to be the one to have that conversation with her, since he and I were going to be around each other a lot more going forward, and it wasn’t something that could just stay hidden indefinitely.

Jessy: I don’t think I’d fully registered how serious or awkward the whole situation actually was until she said that to me directly. I’d actually considered asking my sister’s blessing before making any real move on Lauretta, but the way everything unfolded that night at the party just didn’t leave room for that kind of careful approach. Still, I knew deep down the conversation had to happen eventually; there was no getting around it.

When did you finally tell her?

Jessy: Three weeks after we became official. She was abroad for a short course at the time, which honestly made it a bit easier. I texted her, casually asked how Lauretta was doing, and she waved it off at first. She said she guessed Lauretta was fine, that they hadn’t actually spoken in months. Then she asked why I was even asking about her, and I just blurted out the truth instead of easing into it.

Shoot.

Jessy: She was more disappointed than outright angry, honestly, which almost felt worse in the moment. She said it was weird and not cool that I’d end up with someone she’d been with, even briefly. I sent a longer message explaining things properly, including what Lauretta had told me, that nothing particularly serious had really happened between the two of them. She never responded to that message at all.

Lauretta: The weird part is, even though I knew what was going on to this day, she hasn’t reached out to me at all, not a single message. For some reason, I was expecting a call or angry text after Jessy told her, but it’s been complete crickets. I think she blocked me everywhere at this point. Actually, she has. I don’t see her posts anywhere, even though I see them when I’m using Jessy’s phone.

What about you, Jessy? What’s the dynamic with your sister like now?

Jessy: Things have been a little awkward, though it’s not glaringly obvious since she’s still abroad. We still text and call each other sometimes. But I can tell she’s still nursing some anger beneath all that surface normalcy. She’s coming home this December, which will be the first time we’ve seen each other in person in almost a year, so I don’t quite know what that reunion will look like yet.

Got it. Despite all that, how would you both describe your relationship with each other?

Jessy: Honestly, it’s been genuinely beautiful outside of all that family drama. Lauretta is easy to be around; we can sit in silence or talk for hours and both feel comfortable. She’s also really attentive. I could mention something in passing and she’d bring it up weeks later. I find that really sweet.

I do get worried sometimes when I think about her past relationships with women. I also sometimes worry that she might just wake up one day and decide she’s done with a guy. I’m learning that’s one of the cons of being with a bisexual person. But I’ve made a conscious decision to focus on the present rather than overthink or change anything about who she is.

Lauretta: I’m focused on the present too, for what it’s worth. Jessy has proven to be someone I could genuinely see myself settling down with long term, so that’s really where my mind and attention is going right now. I do wish things between him and his sister could eventually be repaired, though, because I honestly have no idea what to expect when the three of us end up in the same room together for the first time. Outside of that, I have no complaints. He’s reliable, funny, and I’m glad he’s in my corner.

On a scale of 1 to 10, how would you rate your love life?

Jessy: I’d say an 8. What we have is genuinely good, but I’m knocking off a few points because of the unresolved tension with my sister; it’s a shadow hanging over an otherwise solid relationship.

Lauretta: I’ll say 8.5. The relationship itself has exceeded what I expected going in. We celebrated our anniversary last month, and I look forward to celebrating more years together.

*Names have been changed to protect the identity of the subjects.

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