Dating After Divorce in Your 20s

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Dating again after a breakup is always daunting. After the initial flurry of excitement at the prospect of meeting someone new and the confidence boost of a new haircut, the reality sets in that, actually, you are looking to find a connection with someone new that perhaps took you years to build with your former partner.

If you have children, however, you’re also painfully aware that that connection must not just be between you and your potential new partner but also with your kids. “How soon do I mention it?” “Will they like him?” “Am I moving too quickly?” — all of these questions will no doubt be running through your head before you’ve even set foot on a first date.

I divorced in my twenties when my two boys were just toddlers. It wasn’t all plain sailing — I remember one particularly charming guy remarking that being divorced and having children made me “damaged goods.” However, my kids also provided me with a filter for people that simply weren’t worth the effort. Clearly this man wasn’t right for me and his delightful comments helped me to realize that early on.

However, there were times when I found myself in the deepest depths of insecurity about my ability to move on, and I worried that I’d never find someone that would love both me and my boys. The fact that my peers were meeting people and getting engaged for the first time made me feel all the more alone, I was the odd one out.

So, if I had to do it all over again, what advice would I give myself?


First things first, take a deep breath. A first date is just that — a first. It’s a chance to see whether you get on with someone, to enjoy an evening together and think about whether you might meet them again. It’s not a commitment to embark on a new life together. We can become overwhelmed with panic about the future when all we should consider is what’s happening right now. So relax, enjoy and try not to think too far ahead — you’ll just drive yourself crazy.

Be honest

It is worthwhile being straight up with your date about having children. This doesn’t mean saying, “Nice to meet you I’m divorced and have two kids” but it should mean telling them sooner rather than later. It’s part of you and it’ll come out soon anyway. I remember going on a date in a trendy bar in Hoxton, I was trying to be my coolest and most perfect self when my bag fell off the sofa and out fell — a small black and white plastic cow. I said “you should never go anywhere without a plastic cow — you never know when you’re going to need one” — but my cool was definitely blown.

Be prepared for them to be taken aback by this information — it’s understandable that it might come as a shock — and let them know that you’re happy to talk about it. However, you can’t escape the reality that your new partner must be accepting of your situation and if they’re not, it’s simply not going to work. Don’t beat yourself up — dating can be a numbers game whether you have kids or not.

Communicate with your children

Timing is the most important thing to consider. Introduce them to the idea slowly — don’t let them know just before the doorbell rings that someone new is in your life. If you talk to them about your new partner, they may start to develop an interest, ask questions, and may decide themselves that they want to meet them. Ultimately, you know your children better than anyone else and you know how they respond to things.

Share your feelings

It can be hugely isolating when none of your friends are going through the same thing. Our twenties are a time of transition, and it’s not unusual that whilst one of your friends is still living at home with their parents, another is married and having children. Everyone is experiencing something different but that doesn’t mean that your friends aren’t able or willing to offer you a shoulder to cry on even a piece of advice you hadn’t thought of. Be honest with your friends and family about how you feel — you never know when you’ll see something in a completely new light. Just keep it out of earshot of the children.

And don’t despair! Just the fact that you married once makes you statistically more likely to marry again. So take it easy, have fun with your kids and with your own life and interests, and love comes along when you least expect it.

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