The first few dates with your cougar conquest will probably involve dining and drinking at some point. Don’t expect her to pay just because she’s older and financially better off than you are. She’ll appreciate it if you at least offer to pay – it can make someone feel special and cared for, so do be prepared financially for this eventuality. You both might decide on going Dutch, but it’s always nice to be treated from time to time. On the other hand, don’t absolutely insist on always paying – a cougar lady might have been in a one-sided relationship where her former husband held the purse strings. Her financial independence is something she enjoys; she might want to take the initiative and treat the bloke for a change. Whatever the scenario, don’t be afraid to discuss money before the date to save spoiling the atmosphere with awkward fumbling embarrassment over the bill on the night.
Your mature cougar lady might expect certain behaviours that you’re not used to with younger women. Do be chivalrous and open doors for her, and offer a compliment about her attire. Don’t stare at her boobs – keep those eyes above her neckline to show some respect: Although cougar toyboy dating can often be more sex-orientated than more conventional relationships, she doesn’t want to be treated like the raspberry tart you’re having for dessert – at least not over dinner. Drinking too much is also a no-no – it won’t impress. Younger women might be slinging back shots and be happy to drink you under the table, but cougars are more classy than that.
If sex is on the cards then be prepared. Cougar toyboy dating is likely to be centred around sex and you might not be the first young man in her recent history. STIs are rife among your own age group and growing in the middle-age group, so do use ‘something’ – don’t expect to go bareback just because the risk of pregnancy is lower.