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Saturday, November 8, 2025

Can I Date a Guy Who’s Close To My Ex?

DEAR JUMAI,

HELLO Jumai, I need your thoughts on this. I recently met a guy online who’s interested in me. We haven’t met physically yet, just on social media. But the issue is, I found out he is close to my ex, they have this boss–friend kind of relationship. The problem is, my ex and I did some crazy things in the past, and I’m scared he might tell this new guy about it.

Because of that fear, I’ve been holding back from giving the new guy much attention. Honestly, I don’t even know what to think. It feels like it could be a setup.

Back when I was dating my ex, this new guy knew about it, though we never met in person. He would just drop me a DM occasionally, “hello” or “hi”, nothing more. Now that my ex has a new girlfriend, this guy has suddenly reached out to me more seriously.

For context, I’ve known him on social media even before I met my ex. I like him, and I’m currently single, but I don’t know if it’s wise to take things further. Sharon

Dear Sharon,

I understand your hesitation. When there are past secrets involved, it can feel like you’re stepping into something risky. But the truth is, your past doesn’t define your future, and if this new guy is genuinely interested, he should want to know you for who you are now.

If your ex decides to speak about your past, that says more about him than it does about you. What matters is whether this new person respects you, values you, and can build trust with you.

Don’t rush in; take time to observe his intentions and see if he truly wants something real. Don’t let fear alone be the reason you hold back from something that could bring you happiness. Sharon

Everyone’s Finding Love Except Me

DEAR JUMAI,

HONESTLY, I’m exhausted with this whole dating thing. Every time I think I’ve found someone I connect with, it either fades away or turns out to be nothing serious. Then I go online and see all these posts like “Where’s your soulmate?” or “Have you found love yet?” and it stings, because my answer is always no.

I won’t lie, it bothers me. I do want love. I want a real connection. Not ghosting, not half-effort, not games. Just mutual, honest, deep love. Is that too much to ask? I feel like I’ve been putting in the work, showing up, trying to be open, but it still leads nowhere.

And the loneliness is heavy, not just the “oh, I’m single” kind of lonely, but the type that makes you question if you’re even lovable at all. Maybe this sounds like a rant, and maybe I do sound bitter, but at least it’s the truth. And I know I’m not the only one who feels this way. Faith

Dear Faith,

Your honesty is refreshing, and I can feel the weight of your frustration. It’s not easy to want connection so deeply and feel like it keeps slipping through your hands.  But please remember, being without love right now does not make you unworthy of it. Sometimes the right person simply hasn’t crossed your path yet, and comparing yourself to others only makes the wait feel heavier.

Use this time to pour into yourself, to enjoy your own growth, and to stay open without lowering your standards. When love shows up, it won’t feel like you’re begging for effort; it will flow, and you’ll realise the wait wasn’t wasted.

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