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Seeking Guidance on Repentance, Boundaries, and Marriage After a Past Haram Relationship

Assalamu alaykum, I’m nervous to share this so please be gentle in replies. I’ll keep it as short as I can though it’s a bit long. To cut a long story short, I was in a haram relationship for about a year before we ended it a few months ago. At the time we both justified it by saying we’d marry after graduation (we’re both Muslim), but SubhanAllah over that year I learned a lot more about my faith and the guilt grew until I ended the romantic part. We still plan to marry, and we agreed to stay friends while sincerely repenting. Back then I thought that was okay, since we’re very close and best friends. Lately I’m rethinking that choice. We were steady at first, but in the last month we’ve started slipping back into flirting and the same kind of interaction we used to have. It was so gradual I didn’t even notice until a few days ago, and now I have a lot to reflect on. a) I feel foolish for trying to have it both ways. If my goal was true repentance, I should’ve stopped all contact immediately given how the relationship began. b) I’m questioning if he’s really right for me. He’s one of my best friends, compatible with me in so many ways, kind, calm, and I can’t imagine marrying anyone else. But I’ve heard that someone who’s meant for you will draw you closer to Allah, while someone who isn’t may pull you away. In many ways I think this relationship pulled me away-he initiated much of the flirting and physical contact (I wasn’t forced, I made choices too), and my iman suffered for long stretches. Recently my faith has been low and the barakah in my life felt reduced since the relationship started: I fell behind in my career and everything takes so much more effort. Maybe I only started learning seriously about Islam because of that relationship, so it could be unfair to blame him entirely. Still, every step back to the straight path has been started by me, and that bothers me. Now he plans to approach my father about marriage at the end of Ramadan. I love him and want to marry him, but neither of us seems spiritually ready. If we’re still slipping into old habits, I don’t think we’ve sincerely repented. I want Allah SWT to be first in my marriage, and we can’t truthfully promise that if we keep prioritizing our desires over Him. I also worry that a marriage begun like this and with only mediocre repentance won’t have barakah. I’m leaning toward telling him face to face that I love him and want to marry him, but we must get right with Allah first and put Him first, which means stopping all non-essential contact until we’re truly ready for marriage. My questions: 1. How can I bring this up with him in a way that’s Islamic and sincere without sounding like I’m avoiding him or lecturing? 2. Given what I described, is pursuing marriage with him still worth it? 3. What should our contact look like going forward? We can’t keep talking like before, but we also need some way to assess whether we’re ready for marriage. Any advice would mean a lot. JazakAllahu khairan and sorry for the long post.

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Gently tell him you need to pause romantic stuff to focus on Allah, and propose a halal-engagement-style period with supervision. It’s reasonable and loving. If he refuses boundaries, don’t ignore the red flags. Sending dua and strength ❤️

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I was in a similar spot - setting strict boundaries saved me. Tell him you need a space to rebuild your relationship with Allah before anything else. Ask for respect, not lectures. If he truly wants halal, he’ll cooperate.

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I’d say don’t rush. If you both keep slipping, marriage won’t fix that. Ask for a clear plan: no flirting, regular check-ins with a wali or imam, and a timeline to prove change. If he agrees and follows through, that’s a good sign. Stay firm, sister.

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Be honest: say you want marriage but only when both are spiritually ready. Offer a plan: stop private contact, meet families, attend Islamic counselling together. That way it’s constructive, not just rejection. Praying for clarity for you both.

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Short and sweet: stop alone time and flirting, involve parents, and make dua. Real repentance shows in actions. If he’s serious, he’ll accept boundaries. If not, protect your iman first. You deserve barakah.

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This hits home. Tell him you love him but love Allah more, and that means stepping back now. Suggest pausing private chats, doing group meetings or family discussions, and seeing an imam together. If he resists, that says a lot.

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You’re not foolish, you’re human. Repentance can be messy. I’d prioritize cutting intimate contact and bringing in elders. Let actions show sincerity. If he’s with you on that, marriage might still be worth it; otherwise rethink it.

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MashAllah for your honesty, sister. I’d be direct but gentle: tell him you need time to heal and improve your iman before any proposal. Frame it as wanting a blessed marriage, not punishment. Stop non-necessary contact and involve family/mentor for accountability. Praying for you ❤️

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