So you’re on the hunt for your very own Ashton Kutcher-Demi Moore moment, or maybe something a little longer-lived. Either way, you’re not the only bloke to venture out of your age group in search for an older woman. In fact, it’s become so common in recent years there are designated dating sites online‚ like olderwomendating.comandcougarlife.com. And while there’s a seemingly endless supply of stupid “cougar” jokes, there’s also a bounty of misconceptions about what it’s actually like to date an older woman.
If you’re genuinely interested, here’s everything you need to know.
1. Meet her where she is
In general, older women tend to have a better sense of who they are, and can be more independent. We’re speaking in broad generalizations here, of course—age doesn’t say much about who you are as a person, and not all older women are the same. Obviously.
But generally speaking, one of the greatest traits women gain as they age is self-assurance. They tend to have higher self-esteem and worry less about their bodies. Ironically, women tend to be more self-conscious of their bodies in their 20s and 30s. In my sex therapy practice, I’ve worked with gorgeous young women who’ve refuse to try certain sex positions simply because they worried about their stomach, thighs, or butt looking “weird.” Middle-aged and older women still have their insecurities, but they tend not to obsess about them or share them quite as much.
Older women also tend to have more experience, so they can be a lot of fun in bed. Many women report they experience their sexual prime in their late 30s and throughout their 40s. Bottom line: You could be in for the best sex of your life.
2. Don’t pursue her just for her age
Don’t chase an older woman for the sole purpose of knocking something off your sexual bucket list. People are not meant to be “bragging rights,” nor should they be fetishized for one tiny aspect of their persona. You should pursue women you’re genuinely attracted to and have a strong connection with.
3. Reassure her
Your lady may initially feel self-conscious about the fact she’s older than you, especially if there’s a major age gap. In short, all that cougar crap online, on TV, and elsewhere is lighting up in her brain. This is why it’s important to make sure you’re not with her simply for the novelty of it. If you’re serious about her, make an extra effort to let her know her age isn’t important to you. Tell her the characteristics you admire about her most and the specific reasons you’re attracted to her.
4. Be prepared for rude questions
If you’re in a serious relationship with an older woman, especially if she’s significantly older, be prepared for lots of blunt questions from your friends and family. There are still a lot of stereotypes about relationships where the woman is older. You may want to prepare a couple of responses to prying friends and family. Be genuine and specific when you explain your reasons for being together. And if they blast you with something insensitive, feel free to turn the tables. If this is a healthy, reciprocal relationship, explain how it has nothing to do with age and everything to do with how you feel about one another.
5. Make sure you’re on the same page
As with any other relationship, it’s important to make sure you’re on the same page about your goals if you start getting serious. An older woman who happens to also be a divorcee may not be so keen on getting married again. Would that be OK with you? If she has kids, are you excited about the prospect of potentially playing a step-father role? An older woman may also not want to have any more kids, or may not be able to.
You may feel like you’re in over your head, but these conversations need to happen—and you’ll be a better man for it.
Vanessa Marin is a sex therapist. Check out her online orgasm course, Finishing School.
