The Top 10 Things Every Midlife Woman Should Know About Dating

When my marriage ended, I wondered if I'd be spending all my free, non-kid time with my books and my cat. There have been weekends when I've done just that, but there have also been long stretches when I've dated up a storm.
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When my marriage ended, I wondered if I'd be spending all my free, non-kid time with my books and my cat. There have been weekends when I've done just that, but there have also been long stretches when I've dated up a storm. Dating in my 50s turned out to be much more fun than dating three decades ago. I don't feel pressured to get a rock on my finger and I certainly don't want more children. I am much more grounded and more comfortable in my skin than ever before and it is these qualities, I think, that have enabled me to enjoy the dating ride. Here are 10 things I've learned about how to do just that.

1. Hone your online dating profile.

If you expect to find your soulmate on OkCupid, you will probably marinate in frustration. Instead, treat online dating for what it is: an invaluable way to learn about yourself and what you want in a partner, love, and sex. But remember: you are selling, not buying. Do not start off with a mile-long list of "I'm looking for" qualities. Not only are you likely to scare people off, but you also run the risk of alienating people with your high maintenance-ness. What you want is to create an experience of a relationship with you that will attract the kind of man you want to be with.

2. Date people you wouldn't normally date.

If you always date older, try younger. If you gravitate toward dark hair, go for blondes. I always dated white-collar, highly-educated men but after my divorce I had a great casual relationship with a handyman. Dating outside your type -- especially if your type hasn't worked out -- will give you a sense of who you are as a single person, without the pressure of "is this the one?"


3. Always wear sexy lingerie.

Wear it everyday, even if you're not going anywhere but the grocery store. You'll feel sexy knowing you're sporting black lace boy shorts under your jeans, whether or not a guy sees them. Think of lingerie as self-care, a way of honoring yourself as a woman.

4. Have a first date uniform.

Have at least one outfit pre-selected, one that you know you look good in, so you're not scrambling through your closet at the last minute trying to figure out what to wear. For me that meant boot-cut jeans, a black sleeveless top, and black high-heeled sandals. A first date is probably not the time to don an entirely new style; you want to relax knowing you look terrific instead of second-guessing your ensemble.


5. Be honest with yourself about casual sex.

Some women can do it. Some can't. There is no right or wrong either way. But if you get emotionally attached the first time you have sex with a man, then you need to wait until you feel there's potential for a serious relationship. If you just want to explore your sexuality, go for it (but be safe) and don't worry what the women's magazines tell you. You're a big girl and you're capable of making your own decisions about sex.

6. Detach from the outcome.

With dating, as with life, you should focus on the journey, not the destination. But make sure you're always in the driver's seat. Don't feel pressured to have sex before you're ready, or a relationship in which you settle. Don't worry about your wrinkle lines, your imperfect past, or your ex. If your date has a problem with any of this, he's not the one for you. Everyone at this age has less than supple skin and midlife baggage.

7. Have boundaries!

Casual dating is not an appropriate scenario in which to talk about your antagonistic ex, your childhood wounds, or your son's pot problem. If the date turns into a relationship, all of this is fodder for discussion and will come up naturally. But if you lay out your emotional cards in the beginning, you will overwhelm your date and obscure all the positive things about you and your life. Early- stage dating is about fun, not a therapy session.

8. Explore your sexual fantasies.

If you've spent the bulk of your adulthood in a long-term marriage or relationship, especially one in which your sex life was Saharan, now is the time to try the things you've only imagined. If you're on the shy side, loosen up with dirty talk. If you're feeling adventurous, take a stroll through a sex shop. Or a sex club. The only rule is to respect your limits, and those of your partner. But don't get to the end of your life regretting the kind of sex you never had.

9. Be positive.

Your ex may make Attila the Hun look like a nice guy, but don't disparage him over cocktails. And don't trot out a laundry list of the other people who have wronged you, or go on about how much you hate your job. You shouldn't be Pollyanna, but being positive about yourself and others is an incredibly attractive quality -- ultimately much more important than your looks or what digit your age starts with.


10. Enjoy your lack of commitment while you can.

Don't be miserable that you're not in a relationship. And don't kid yourself that all those married couples on Facebook are living in blissful unions. You may not have a date for Saturday night, but then you also don't have to deal with someone else's money problems, health problems, or failure-to-launch kid problems. Nurture yourself in your alone time: start that yoga practice, take a cooking class, write a blog. And enjoy dating for what it is.

Practice for the real thing.

Photography by Nick Holmes and Inez Lewis

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