Dating an Older Woman

Sometimes age doesn’t matter and other times it makes all the difference. An older woman offers experience and stability and is less likely to play mind games. But dating her comes with caveats. Here, some rules of engagement.

When You’re in Your 20s and She’s in Her 30s
SEX: Sure, you’re good in bed, but a woman in her 30s likely has more experience than you. While a younger lady may be shy to point you in the right direction, an older woman often has no problem telling you where to put it. She may want to take the lead — let her. Learn from her. Many a man has taken away advanced techniques from an older woman.

MONEY: So, say she always offers to pick up the tab, whether or not you’re still paying off student loans. It’s tempting, and maybe she’s generous, or maybe she wants to eat at restaurants she knows you can’t afford, but, she will likely lose respect for you if you always accept freebies. Take her out once in a while; neighbourhood pub’s fine, skip the Michelin Guide.

COMMUNICATION: The casual courting you may be accustomed to with a woman your own age — meet at a party, hang out with mutual friends, make out after the bar — might not work here. Neither is a woman in her 30s as likely to waste away every weekend partying with your posse and sleeping late in your bed. She has her own life and established social network; don’t expect her to share what she’s doing every night. (Note: could be an advantage if you want only a fun fling.) She’s also likely either eager to find “the one” and start a family or have a fun fling with a “young buck.” Both of you should be clear about what you want here, up front.

When You’re in Your 30s and She’s in Her 40s 
Expect Commitment
SEX: Surely, every city has its Samantha Jones (the 40-something Sex and the City character who loves sex without commitment and shuns monogamy), but most women this age want a life partner, if not a family. You probably won’t need to do any detective work on this front; 40-something women long tired of playing games and most will be candid.

MONEY: A woman in her 40s may have a great job, make excellent money and own property. If, in your 30s, you’re not there yet, no worries — just make sure you have clear sight of your aspirations and a plan to achieve them. She’ll want to know you have direction (and it’s good for your future, anyhow).

COMMUNICATION: In the modern workforce, many 40-somethings are on a second career and have already enjoyed all the top restaurants in town. Be prepared to be intellectually challenged and enjoy lots of stimulating conversation. Don’t see it as competition, and don’t underestimate what you can bring to the table. Look at it as what it is: conversation. Commonalities will reveal themselves. If you are intimidated? Treat it like poker, and don’t show it.

When You’re in Your 40s and She’s in Her 50s
Quoth the bardette Aaliyah, Age ain’t nothing but a number.

Image via TechCrunch50-2008.

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