Dear Richard Madeley: ‘An older man sends me gifts after we have sex – it’s icky’

present in red ribbon on desk
'It's impossible not to see them as payment in kind for services rendered' - Moment RF

Dear Richard,

I am in the early stages of a relationship with a slightly older and much better-off man. We have spent the night together maybe half a dozen times. Each time he has sent me a gift: a pendant, flowers sent to my office, a pair of gloves and so on. A couple of them have touched on things we were talking about the previous evening in a nice, attentive way.

But so neatly do they seem to coincide with the occasions when we have had sex (a few times we had dinner together and then went our separate ways, and no gift was forthcoming) that it’s impossible not to see them as payment in kind for services rendered. (I should say our physical relationship has developed slowly, tentatively and with complete courtesy and respect on his part.)

Naturally, I find this somewhat icky, not to say weird. It’s possible that he thinks he’s being romantic or that his relative wealth obliges him to be generous, but I’d like him to stop. So far I have said thanks and changed the subject, but I do want to talk with him about this rather than just walk away; I suppose I have been waiting for the relationship to feel more secure before raising a potentially awkward subject. Can you advise me please?

— Ella, via

Dear Ella,

Yes, I’m not surprised you’re unsettled by his behaviour. It is a bit peculiar, however well-intentioned. If he sent you these little gifts after every date, it might feel less transactional. But the fact these goodies arrive only after you’ve had sex must be pretty disconcerting.

I suppose he might say it’s simply his way of saying ‘thank you’ – but that makes the sexual arrangement seem oddly one-way, as if you’ve done him some kind of special favour. (I wonder how he’d feel if you sent presents to him after these evenings together?)

Look, Ella. The only way to resolve this is to tell him how these post-intimacy gifts are making you feel. Ask him why he seems compelled to send them to you. It will be awkward, but if this relationship is to have a future, you’ll need to be able to talk about things – however uncomfortable. I’m not sure what he’ll say but I’d be very interested to find out. So do write to me again. And good luck.

You can find more of Richard Madeley’s advice here or submit your own dilemma below.