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Taking On a Younger Man - Cougars Confess Their Secrets

Dating a younger man? Are you serious?!

Older women/younger men dating has exploded in recent years. More women than ever are breaking free of ‘traditional’ relationship norms and experiencing the exciting world of cougar dating.

This dating niche is most attractive for women looking for thrills in their relationship, compared to the routine and mundanity traditionally seen in relationships with older men. It’s a dating scene for women looking to spend their evenings salsa dancing with a gorgeous younger man, instead of an early night in with Captain Boring.

It’s a dating scene for women not looking to settle, who want to explore everything new; from the wider world to their sexuality. Whether you’re a woman interested in dating a younger man in your 40s, 50s or beyond, it’s easy to see why more and more women are looking to enjoy the thrills of age-gap dating.

this woman knows how to date a younger guy

Is there a ‘but’ coming when it comes to dating younger men?

Like with any dating niche, there’s the studs and the duds. There are guys looking to excite your dating experiences, and others looking for a cheap, unexciting fling. We’re going to show you how to separate the wheat from the chaff. How to find the most charming younger men and how to bag them.

The following is dating advice and insights from members of cougar dating site Toyboy Warehouse. We interviewed women who’ve successfully found love, lust, and romance to ask them exactly how did they do it.

Keep your options open if you want to know how to date a younger guy

Compared to any other form of dating, online dating allows you to keep your options open. It’s not unusual to have a number of different conversations going on at one time. So if you do get rejected by a younger man, it’s not that big of a deal.

The playing field is split between genuine guys and not-so-genuine guys, having more than one conversation going at one time allows you to keep your options open. This is some of the best dating a younger man advice on the planet. It can become very exhausting to invest a lot of time and commitment with one guy, only to encounter a huge red flag and having to cut ties and start all over again.

The easy and non-committal nature of online dating allows you to have conversations with several potential partners. So that if a dealbreaker comes along, there’s still plenty of other handsome candidates waiting.

Then when one guy starts to become a genuine candidate for your affection, you can focus your attention on just messaging him. Now you’re giving him your full attention, he’ll be even more receptive and grateful. Moving from keeping your options open to messaging that one lucky guy will be a big indicator you want to move things forward.

woman texting younger guy

You message about the insignificant

A lot of people forget online dating is supposed to be fun. If it starts to feel like a second job, chances are you’re doing it wrong. Meeting new guys, messaging and flirting, this is where you should find excitement, not boredom. You can keep him interested.

If you’re messaging a handsome younger man, have a think about how the conversations make you feel. Are they fun flirting or do they feel like you’re taking part in an interview? Are they overly serious or carefree and playful?

A big indicator is whether or not you message about the insignificant, and it’s still fun. Because online dating is so messaging-focussed, it’s very easy to run out of things to talk about. So if you’re chatting about the little details of each other’s lives, and it’s still enjoyable - then you’re onto something special. Did you two have a laugh about that picture he sent of that guy at the bank with the worst comb-over ever? Did you playfully tease him about spelling guacamole wrong?

These are the moments where genuine connections are formed. He’s casual, not intense, calm not overly passionate. Starting a relationship with this guy will be easy and enjoyable, not a drain on your energy.

How do you attract a younger guy online?

Online dating can differ from site to site, but there’s a number of things that remain the same. One of those being profile pics, every dating site uses them in some way. To attract the right guys, you'e got to have a great online dating profile. 

Not only do profile pictures help you determine whether or not you’re sexually attracted to a certain younger man. It’s also a good way of seeing the level of commitment a guy is willing to put into finding and maintaining a relationship.

It’s very easy to join a dating site, enter a few details and away you go. This means many people may join on a whim, with no intention of being the charming, exciting younger man you’re looking for. A good way to see if a potential dating candidate is willing to put in the commitment is taking a look at how many profile pictures has he got. Did he just throw up one or two poorly selected pictures? Or did he take the time to choose at least four photos that show off his personality and appearance?

How about his bio? We’re not looking for War and Peace, but it should sufficiently describe himself in a fun and flirty way. Enough to have to something to start a conversation with but not too much it start becoming overly intense.

If a guy is willing to commit to building a good dating profile, he’s much more likely to commit to a relationship with you.

young guy hanging out at office

If he tries to make you laugh . . .

He probably likes you. Remember, he’s trying to woo you. Part of online dating is the chase, it’s him trying to impress you with his personality, wit, and charm. Age-gap dating is no different. You’re not any less deserving of the chase because you’re the older woman, if anything, you’re more deserving of it. Remember, you have the experience, the confidence, and the foresight to know what you want from a relationship. If a guy isn’t making the effort to try and impress you at this stage, he’s definitely not going to put in the effort later in the relationship.

Don’t get me wrong, the poor guy doesn’t have to walk over hot coals for you. His efforts to impress you, while sweet and lovable, may fall flat. But as long as he puts in a level of commitment and effort at this early stage and you genuinely fancy him, then he should definitely be a contender for the title of your next boy toy.

Now what...?

So you’ve done your due diligence, you’ve sorted the agreeable from the atrocious, now how exactly do you bag yourself a handsome younger man?

Reward him as you see fit

Guys, especially younger men, love to feel important and listened to. That doesn’t mean you need to give him your constant undivided attention, but it is something you can use to attract him.

If he acts in a way you don’t like, he becomes distant or non-committal, take away your attention. When he acts in a way you do like, he starts flirting or being complementary, then give him your attention as a reward.

If you want to reward his ‘good behavior’, show interest and curiosity in his opinion. That’ll be sure to make him warm to you, helping to start something really exciting with a handsome younger man. Of course, if he’s a giant bore, forget about showing interest in what he has to say, it’s probably best to move on.

Take note of the difference between ‘hard to get’ and ‘ghosting’

The age-old advice rings just as true, you don’t want to be overly eager. You don’t want to appear desperate or clingy, online dating should show you off as cool, sexy and confident. So a little ‘hard to get’ isn’t a bad thing.

Remember, hard to get is different in online dating - especially if its early days in your relationship. If you’ve seen each a number of times, a few days without a call or a text is playing hard to get. If you’ve only been messaging, a few days without a message may be seen as a sign that he should move on.

Ghosting’ is where one individual just stops all contact when online dating, it’s common enough that it’s pretty easy to take the hint. If you don’t message or reply to a message for a number of days, it’s more likely to be taken as an attempt to ‘ghost’ him than to entice them.

Play hard to get but keep a consistent level of messaging, be flirty and teasing but don’t disappear off the radar unless you’re not interested. Get him to put in the work. Remember, as an older woman in the relationship, he’s looking to you as a confident, sexy potential partner. Use this to your advantage.


sexy business guyDon’t be afraid to be forward if you’re dating a younger guy

Now as a confident, sexy potential partner, allow yourself to not be too afraid to move things forward. The traditional is out the window. You don’t have to wait for him to ask you out if you want a date. If you want a wild evening of romance, it’s yours for the taking.

As an older woman, you’re more likely to know exactly what you want. Younger guys are aware and receptive to this, they’re more eager to please and are willing for you take the lead. Embody confidence and get exactly what you want.

If confidence isn’t your thing, take solace in online dating. The dating medium allows you to explore the parts of your personality you might be more afraid to explore in traditional dating. If you’re not the most confident but you’re keen to improve that, have fun playing confident online. You’ll be amazed how easy it is to become the bold, seductive older woman you’ve always wanted to be.

Go get ‘em girl!

Ask anyone in the dating scene, age-gap dating s an exciting and exhilarating niche you need to explore. If you’re looking for love, lust, and romance with a younger man, just remember, it’s there for the taking. With a little due diligence, some flirting and a whole load of fun, you can bag yourself a handsome younger man. If you want to attract a guy using the law of attraction, check this out! 

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