How to help nearly 5yo with separation anxiety

[TheEveningSun]

My DS is quite a sensitive child. He doesn’t like being away from me. He’s in reception and really struggling with saying goodbye but has a good time when he’s there. He says he doesn’t want to attend after school activity because he just wants to be home with me.
Before he started school he was in a nursery 2 days per week since he turned 1. When he’s with me we always go out and do something fun. Nursery drop offs were mostly dramatic. there were good periods too. I also have a 2.5yo DD.
Myself and DP go out 1-2 times per month, my DS loves his babysitter and even though it was never easy for us to leave the house, recently he goes hysterical when we go out or when I go out by myself. Nothing I say to him calms him down. Explaining we’d be back in couple of hours or that mummy and daddy need a play date with our friends just as he needs his. He just doesn’t want us to go out.
Generally he’s a very confident and outspoken child when 1:1 play dates with his friends but gets overwhelmed at parties. It used to be hard for him to join the party fun with others. Now it’s changed and he runs off with everyone to play.
We have a strong bond so maybe he’s getting used to being away from me with 5 days school. It’s just so upsetting to see him struggle so much when we go out.
He’s always been a bad sleeper so in 5 years me and DP had only 1 night away from the kids. It didn’t go well either. He woke up at 3 am and decided to wait for mummy to come back. He lasted till 2pm!!
How can we help our DS with his separation anxiety? Why no amount of reassurance helps? We talk to him before going out he seems ok and understands but when he sees me at the door ready to go he gets so upset. He’s fine when I leave them with the babysitter during the day. It’s just the evenings and school drop offs. I’d appreciate your advice 🙏🏼

I hear you, and I understand how tough this is, not just for your son, but for you as well. Separation anxiety can feel overwhelming, and it's not something that just goes away with a quick fix. It’s an emotional experience, especially for a child who’s sensitive and attached like your son. You're right—this is a really tough time for him, and it's not something that can be dismissed with simple routines or quick tips.
Acknowledge his deep feelings: Separation anxiety for a child can feel like a real fear of being without the person they depend on most. Even if he's having fun once you're gone, in the moment of separation, it’s like his world is shaking. Instead of trying to brush it off with explanations, sometimes just sitting with him and acknowledging, "I know it’s really hard for you when I leave, and it’s okay to feel sad," can help him feel understood.
Slowly build his tolerance: Some kids just need more gradual steps. Since he’s okay with daytime separations, try small, low-pressure separations in the evening—maybe start with just a 10-minute walk where he knows you’ll come right back. Gradually increase the time as he gets used to it.
Comfort object or "connection ritual": Give him something that reminds him of you when you’re away, like a small item or a note in his pocket. You could also create a “goodbye ritual,” like drawing a heart on both of your wrists so he can press his when he misses you, knowing you're doing the same.
Consider what might be triggering the anxiety: Sometimes the start of school or any changes in family dynamics (even with a younger sibling needing attention) can amplify these emotions. It could be helpful to talk through what's worrying him in a non-rushed, calm setting let him lead the conversation and try to identify if there’s something specific bothering him.
It’s normal that no amount of reassurance seems to work right now he’s going through a real emotional struggle. You’re already doing an amazing job by being there for him.

Thank you for that! It’s very helpful, i love the heart idea ☺️ will definitely try it. Apart from that I do pretty much everything you mentioned. I do sympathise and say I know how hard it is. Can’t figure out the root of the anxiety. He just keeps saying he wants to be home with me. Hopefully it’s only temporary

@TheEveningSun You're doing an amazing job by being so supportive and empathetic. It's completely normal for kids to go through phases of anxiety, and I truly believe that with your love and patience, things will get better. Sometimes it’s hard to pinpoint the exact cause, but just knowing you're there for him can make all the difference. Hopefully, this phase is temporary, and with time, he'll become more comfortable and secure. One day, he will understand how much you’ve helped him through this, and things will feel easier. You're both going to be okay!