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Where and How to Meet Older Women

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Q: I wanna try an older woman as I am nineteen, but I don’t know what to do. I have had a few girlfriends, but I didn’t know how to make a move as I was too shy. I don’t know where to find older women or how to get out there. Any ideas? – R

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A: Thanks for writing and sharing your fantasies with us. I have no doubt this one and all of them will come true! Don’t worry about being shy or about not having had all the experiences you’ve wanted.

You are just at the beginning of your lifelong erotic journey and even though you’re horny and ready to get on with it, that sense of urgency is normal… and very exciting. Take your time, and enjoy the sexy thoughts you’re having while you figure out the dating and hook-up game.

You might be surprised to learn that lots of people are shy about making moves with a woman, including me! With practice I’ve become very comfortable in my skin, but I still get tongue tied around women, even though I’m not that shy when I see a man I want.

Online dating is a really great way to meet people because you can put it all out there and the approach tends to be a volley back and forth with messages until something clicks, rather than having to just go up to someone you see at the mall or in the pub.

There’s no harm in writing in your online dating profile that you’re shy, because there are lots of shy women who might feel more comfortable knowing someone else is nervous too. Be careful that saying you are shy AND stating your desire to hook up with older women might send a signal out to creepy cougars that you are vulnerable and easy to take advantage of. Women can use guys too, and you want to be cautious about being misled by your feelings if an older woman considers you prey.

So even though I usually think the best approach is to state it all in your profile and see who connects with what you are looking for, I would actually recommend in your case that you create a nice, honest profile but leave it open to meeting all kinds of women.

Chat a lot with anyone you feel a physical or other connection with, and go out on some dates. Don’t specify that you are dying to meet a mature woman for sizzling sex. Instead, see who you meet and enjoy all of it.

Then, in order to fulfill that fantasy AND get comfortable with “the approach,” YOU can reach out to hot mature babes you see. In your message to the cute cougars you see in profiles, just say something honest like, “I’m a young dude and was taken with your profile pic. I’ve had a lot of fantasies about meeting an older woman and wonder if you’re open to meeting a young guy like me.”

Make sure the women you’re reaching out to are looking for casual fun, not posting in search of a man to start a family or a long-term relationship. Don’t be disappointed if lots of them don’t write back—just keep trying. Some won’t be comfortable having sex with a young guy, but don’t worry, you’ll be meeting other women too and building your confidence and dating game.

Have a blast and let us know how it goes!

Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex, we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter.

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