Re-entering the dating game is not for the faint of heart. For proof, you only have to look at Vanessa Feltz. Engaged to the singer Ben Ofoedu from 2006 until 2023, she has since been providing a vital public service in chronicling her dating disasters as a lesson for the rest of us. Her latest learning? Beware the seemingly suitable man.
After a tortuously tedious date with a younger man (‘I had really lost the will to live’), Vanessa allowed herself to be matched with men her own age. ‘We go for a suitable age, suitable consort, but they don’t seem to have an ounce of game or banter or humour or flirtation,’ she told The Sun. In fact, she suggested, they seem to think ‘it’s a big achievement to be still alive’.
Why dating is harder in mid- and later life
Vanessa’s frustration is not unusual, suggests Dr Tracy King, a chartered clinical psychologist. ‘Many women over 50 are no longer willing to generate all the conversation or direct the next date or stage of the relationship. They may have carried the invisible load in prior relationships and have had enough now. A new relationship needs to add to their life, not take from it.’
They have every right to be discerning, agrees Jeanne Sullivan Billeci, dating expert and coach at The Soul Mate Coach: ‘They have lived enough life to know what does not work for them and many have survived painful relationships, divorce, betrayal or years of feeling unseen. They are not being “too picky” for wanting something better the next time around.’
But does that make dating as a fully fledged grown-up just an impossible task? No, says Jeanne: ‘I coach a lot of women over 50 and sometimes they’re focusing on the wrong qualities instead of those that would make them feel safe and happy in the long term.’
‘The challenge is that healthy discernment can sometimes become hypervigilance,’ she explains. ‘In trying not to repeat the past, women may look for absolute certainty on the first few dates or dismiss someone quickly because he does not immediately match the romantic picture they had in mind.’
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When too much ‘game’ is actually a red flag
Older men may sometimes lack polished ‘game’ or ‘banter’ simply because they’re a bit rusty after emerging from a long-term relationship, says Dr King. This needn’t mean there’s no relationship potential: ‘A person may be skilled at creating attraction without being capable of consistency, intimacy or repair. Likewise, a man who is nervous or unpolished may possess precisely the qualities needed for a secure and safe partnership.’
That does not mean you should lower your standards, stresses Jeanne. Instead, it involves distinguishing between a man who lacks game and a man who lacks relationship skills. ‘Banter is lovely,’ she summarises. ‘Emotional availability, curiosity and reciprocity are what sustain love.’
Be a dating detective
Dr King suggests the following approach: ‘Treat the first three dates as evidence-gathering, rather than settling on a verdict, unless there are any safety concerns or clear incompatibility. Ask yourself: “Do I feel respected? Does this person do what they say? Can we be curious together? Do I feel more or less myself with them?” And let your answers contribute to your choices.’
Choose compatibility over spark
Compatibility is quite different to spark, says Nicole Everingham, a relationship and dating coach. The former ‘is something we discover and build as we get to know someone – how well your values, needs and lives fit and how you navigate the places where they don’t’.
It also, crucially, doesn’t mean you never disagree. ‘What matters is what happens when you do,’ she explains. ‘Can you talk, listen, repair misunderstandings and remain respectful when you see something differently?’ It might be less fun than banter, but it’s a better long-term recipe for dating success.
Dr King’s 5 strong indicators of compatibility later in life
1. Alignment on values and the way everyday life is run, rather than just shared hobbies
2. Consistency between words, actions and availability
3. Curiosity about you, rather than selling themselves and trying to impress
4. Ability to take responsibility and repair ruptures after misunderstandings
5. You feel able to remain yourself, rather than feeling like you’re auditioning for a role
...and her 5 warning signs
1. Contempt about former partners
2. Small boundary pushes, especially with a sense of entitlement
3. Premature intensity and quick attachment
4. Erratic communication
5. Inability to apologise
