Tips for dating after being single for a long time

Our agony aunt Mary Fenwick shares her advice for one reader who is thinking about dating again after being single for a long time...


dating again after being single for a long time

If you’re thinking about dating after being single for a long time, taking those first few baby steps into the dating pool can feel pretty daunting – especially when the whole world of romance seems to have moved online.

Does the idea of dating currently make your insides coil up? Don’t fret: you’re certainly not alone. Dating can be tricky even for the most outgoing of people – you’re putting yourself out there in a vulnerable situation, after all. However, with a few confidence-boosting tips, anyone can successfully navigate the world of modern dating and find love again.

Below, our agony aunt Mary Fenwick shares her advice on dating after being single for a long time, in response to one reader who is hoping to dip her toes back into the dating pool after being a single parent for 18 years…

dating again after being single for a long time

Should I start dating again after being single for a long time?

‘After 18 years as a single parent, I had almost convinced myself that I did not need anyone additional in my life. But with both my children now in their 20s and living independently, recently, close friends – who all have partners – have suggested I join a dating site. I have a clear idea of the kind of partner I would hope to find, but little confidence that my search will be successful. Should I be brave enough to at least give it a try – or resign myself to a life of bespoke solitude?’ – Anonymous

Mary’s tips on dating after being single for a long time…

I love the way you write: your personality comes across even in this short letter, and I encourage you to bring that into your dating life. Online dating is an efficient way to meet people and, even pre-pandemic, 39 per cent of couples in the UK met virtually, compared to 20 per cent meeting through friends.

Work on your confidence

Social psychology researcher Rachel New uses her scientific and practical experience to help people understand the world of 21st-century dating. She runs an eight-week online programme, which starts with learning to feel good about yourself, and also covers the costs and benefits of online dating, and how to work out what your own needs are.

Rachel suggests the dating app Bumble, which puts women in control of the process (you have to make the first move), as a great place to start.

Know what you want in a partner

Although you have clear ideas at the moment, the things that initially attract us to somebody are not always the qualities that build a deeper relationship.

One example is conflict styles – does the other person sulk, or can they make a relaxed comment about a different point of view? It might be helpful to know that, on average, one in ten first dates leads to a second date.

Make dating fun

In the meantime, how can you make the process fun? Could you create opportunities to try a hobby or go to a concert with someone new? You might even consider a video meeting as a first step, to check that the person seems trustworthy. Do you feel at ease and able to be yourself?

Even though initial contact might be online, it’s the quality of connection in real life that matters. If being able to spend some time in ‘bespoke solitude’ remains important to you, it will also matter to a person who cares about you.

Mary Fenwick is a writer, speaker and executive coach. She is also a mother, divorcee and widow. Got a question for Mary? Email, with ‘Mary’ in the subject line. For more about Mary’s work in leadership and team coaching, her ‘Writing back to happiness’ programme and free resources, go to

More inspiration: How to get over your ex