I’m in my late thirties and have been dating someone a few years older for a few months. He is divorced (he says he was never happily married), and has two teenage sons. He is great fun, intelligent, witty and can be very loving, but I’m confused about boundaries. He talks a lot about his ex, still feels guilty and seems reluctant to let go of other past relationships. He sometimes comments on other women’s attractiveness, usually celebrities. I find this hard and don’t always feel particularly special. I’ve suggested counselling about his past guilt, but he won’t hear of it. On the other hand, he’s very full-on, wanting my undivided attention and time. He’d like me to go on holiday with him and his children, but I’m not sure how “safe” I feel with him. He tells me he loves me, but my guard is up. Just because he had an affair once doesn’t mean he would do it again. I do want to give this a fair shot as I’d like a committed relationship and a family, but am worried that his past is clouding both of us. What should I do?

The message that seems to be coming through is that you don’t trust this man. I wonder why not. Trust involves more than ticking the right boxes, such as fun, intelligent, witty and loving. It is an instinct or intuition, and yours seem to be telling you that things are not as they seem. Now, you could listen to your intuition and decide this is not a goer, but before you do, it might be helpful to ask yourself a few questions. Is it possible you are throwing obstacles in the way of this relationship because of your own deep-seated feelings of insecurity, rather than any sinister behaviour on his part? Asking somebody you have been intimate with for only a few months to go and see a counsellor does seem a rather overanxious response.

I am also puzzled why you don’t feel safe enough to go on a family holiday. It’s your use of the word “safe” that’s puzzling. Again, this seems like such an overreaction to the suggestion of a couple of weeks in the sun that it makes me wonder whether this is more about your feelings of insecurity than his actual behaviour. He’s very attentive, tells you he loves you and has asked you to go on holiday with his children. Now, if ever there were a sign of commitment, it is allowing you to become involved with his children. The only black mark against him seems to be an attachment to women from his past. Are you sure he is excessively guilty about his ex-wife and reluctant to let go of past relationships, or is it more that you wish they didn’t exist because any reminder of them makes you feel insecure? Be really honest.

I wonder if it’s the latter, simply because of your use of the word “special”. He doesn’t make you feel particularly special. Now, I wonder what it would take to make you feel special. Would it be a man who behaved as if his past lovers didn’t exist and refused to have any contact with them, a man withoutthe ability to feel sadness or regret? Or would it be a man with no attachments or emotional history? In other words, what you seem to be looking for is a man untouched by human hand. Nobody turns up without baggage — particularly by the time we get to our thirties — but some people are able to put it safely into storage while others carry it into the next relationship, leaving little space for anything else. It may be that he is one of those carriers. It could be that his baggage is too big to get around. Or it could be that the baggage is actually your own.

You give no clues as to what has happened to you in the past. I wonder if you have been badly betrayed, or whether suspicion and jealousy have always dogged your relationships. Those seem to be your dominant emotions, which is why it’s important to get really honest and work out if these are feelings you are projecting onto him, or whether they are real concerns.

You know I can’t possibly tell you what you should do other than suggest that there are two sides to every story, and that, sometimes, the story is based on a script we have written ourselves. I do, however, think it would be both sensible and instructive to go on the promised holiday. It is always revealing to see how people interact with their children, and teenage boys are famously bad at dissembling.

If your fears about his feelings towards his ex-wife have any basis (and you seem to be implying an unresolved attachment), then her sons will soon reveal what it is. Living in such close proximity — even for a couple of weeks — will give you a fair idea of his true nature. Being open to love and making a commitment involve taking a risk. Here’s your final question: are you fearful about him? Or is it more that you are fearful of loving somebody? You’re the only one who knows the answer.

If you have a relationship question for Sally, e-mail sally.brampton@ sunday-times.co.uk. In case of publication, names will be withheld. We’re sorry, but Sally cannot answer letters personally

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