Reaching out to someone I was close to 5+ years ago - is this email appropriate?
Hey everyone, I (24M) need some advice on a situation that's been weighing on me for years.
Background:
I'm Turkish, living in Rotterdam, Netherlands, and Muslim. Back in 2017-2018 when I was around 16-17, I met a girl online - also Turkish, Muslim, living in Toronto, Canada, one year younger than me. Let's call her Emily, and let's call me Enzo (not our real names for privacy). We connected over our Islamic identity and had deep conversations about religion. We exchanged books through email. Over time, we developed real feelings and started talking about marriage (which is how relationships work in our culture - you talk with marriage intentions).
What happened:
At the end of 2019/beginning of 2020, her aunt visited from Turkey and Emily confided in her about me. The aunt promised not to tell her mom, then immediately did. Her mother got really upset, took her phone away for a week, and when Emily got it back, she explained what happened and then blocked me. I was terrified of making things worse for her with her family, so I didn't reach out.
About a year later, she viewed my LinkedIn profile. I still didn't act because I was paralyzed by fear of rejection.
Why I waited so long:
I know 5 years seems like forever. The honest truth is: fear. The way it ended was traumatic for both of us. I was young, scared of her mother's reaction, terrified of being rejected after everything we went through. I also knew I needed to grow up, build myself, and become someone worthy of reaching out. So I finished my computer engineering degree, got a good job in cybersecurity, worked on myself spiritually and emotionally. Now I finally feel ready, but I'm still scared.
The Email I Want to Send:
After talking with my mom (who helped me a lot with this), here's what I've drafted:
Subject: Checking in
Selamün aleyküm ve rahmetullah ve berakatuhu Emily,
I hope you're doing well and in good health. This is Enzo, from the Netherlands - you might remember, years ago we used to talk about Islam and exchange books through email.
In the years since, I graduated from computer engineering and I'm currently working in cybersecurity. Alhamdulillah, it's been a good journey of growth, both professionally and spiritually.
How have you been? What's your situation?
Fi Amanillah.
Enzo
My concerns:
- I don't know if she's married or not
- I don't know if she still thinks about me or has moved on
- She might ignore this email
- The email needs to be respectful enough that if she IS married, her husband wouldn't have any concerns reading it
My mom helped me keep it neutral and factual - not too emotional, just checking in like you would with any old friend. If she's single and interested, she'll understand why I'm reaching out. If she's married or not interested, it's harmless enough to either politely decline or just not respond.
What I'm asking for:
- Does this email seem appropriate? Too cold? Too warm? Just right?
- Is my approach reasonable after 5 years of silence?
- Any advice for managing expectations? I'm prepared for no response, but it will still hurt.
- Timing question: What time should she receive this email? Morning, afternoon, evening, or night in her timezone (Toronto)? Does it even matter?
I know there's no guarantee she'll respond, let alone respond positively. But after 5 years of wondering "what if," I need to at least try. My mom supports this, which gives me confidence.
Any advice, perspectives, or constructive criticism is welcome. Thanks for reading this long post.
TL;DR: Reconnecting with someone I was close to 5+ years ago after a difficult ending. Need advice on my approach and email before I send it.
Posted Oct 5, 2025, 3:47 PM UTC