How to Start Dating Older Women

Photo:  Robert Nicholas(Getty Images)

Don’t let your infatuation with mature females remain only in the domain of your imagination and internet browsing history, you need to act sooner rather than later as pretty shortly “older women” will mean retired grandmas to you. Life goes fast, and you should make your fantasies of dating older women a reality while you can, as it is a life-enriching experience that every man should have.

Hopefully, these tips will drive you to understand you’re not at a disadvantage as you might believe and will get you closer to your goal.

Start With Yourself

First thing first, you need to begin by getting yourself in order. Of course, you shouldn’t fake who you are, but perhaps the chance of dating older women will get motivated to do things that you already know are good for you. Start with your clothes, as older women don’t want a guy that dresses like an infant in sporty clothes, most of them had to endure that from their ex-husbands too much, while all will just view you as a man-child.

You’ll be surprised how much a classic pair of shoes can make a difference in the way women look at you, combined with a button-downed shirt, or particularly a suit, you’ll appear more mature, yet still youthful. When it comes to grooming, pick between the bearded or a shaven look, everything in between might work for young hipster girls, but not for mature ladies. For them, it will look like you’re lazy to take care of yourself, or even worse, that you’re still going through puberty. Also, while older men can maybe offer them more stability, money or experience, you ought to look better than some guy in his forties, so hit that gym and eat healthily!

Location Location Location

If you just don’t seem to come in contact with a lot of older women, that’s probably because they don’t dwell in college bars where chugging beer is a sport, so widen your horizons to where you spend your time. But don’t just focus on upscale bars or coffee shops, that is too limiting, instead, have the approach mentality wherever you are – the grocery store, gym, in public transit, at work, on the street. Wherever! You might catch a girl off her guard and subtly imply that she looks beautiful to you even when she’s not all dressed up.

Online dating and specialized sites for the dating of older women and younger men like Cougar Life are a no-brainer.

Make the First Move

Most guys are too scared to approach an older girl out of fear that they won’t have something to talk to them about, which is ironic as you’re thinking about dating them, which involves quite a bit of talking. Openers are deemed as the hardest part of the approach but think in the frame of the situation you’re both in and ask her something about what’s she currently doing like working on a computer, glancing at a thing, trying out a pair of pants. Or start commenting something in the environment she might be interested talking about, like the novel she picked up in the book store or that tasty looking lunch she was served.

Stay off pickup lines as she probably heard them hundreds of times, well maybe not these awesome ones, but they are still better for younger girls as most of them are cheezy or inclined for the younger population.

How to Act

Don’t try to hide your youth, as that should be your main point of attraction – you’re young, full of life, optimistic, hungry for new experiences, not jaded like people tend to become with age. This doesn’t mean you should start bombarding her with Foul Bachelor Frog memes but don’t restrain your energy. Also never lie about your age, that’s just stupid.

But youthfulness won’t do you much good unless you combine it with confidence and a sense of purpose. Display that you have your life figured out or at least planned for the most part. One of the keys of dating older women is that she needs to see that you know what you’re doing, both in your own sphere, but also in your relationship with her.

Never act like your throwing a hail mary by approaching her, establish that she is a viable option for you as you are for her. Think positively about the outcome as older women can detect the level of confidence even better than young girls. They might even try to blow you off just to test your insecurities so keep your chin up and don’t fall back at the first jokingly pejorative comment.

The Next Step

After getting her number don’t go and start obsessively texting with her as you’re not dealing with a Millenial, and pick up the phone when asking her out, like in the time way, way before.

Also don’t play games, she’ll probably played them already on hard difficulty and is sick of them. One of the best things about dating older women should be the opportunity to relax from the games and to have an healthy relationship.

Never make a big deal about her age, the chances and the fear are your environment will, so you don’t need to add to the problem by constantly mentioning it, just act like you would in any other relationship.

What are some of your tips for dating older women?

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