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Toyboy and cougar dating success

Three steps to first-date success

It’s the start of a new school year, the perfect time to learn something new, right? Learning’s not just reserved for kids, you know. We can all get stuck in a rut or need to brush up on our skills – and our ability to create great first dates is no exception. So whether you’re an experienced dater, a toyboy just starting out, or a cougar getting back into the dating arena, here’s how to brush up on your first date etiquette. New pencil case optional. It’s the start of a new school year, the perfect time to learn something new, right?


Focus on them

Everyone feels nervous or awkward on a first date. It’s perfectly normal and natural. Meeting someone new leaves us vulnerable to rejection and, hey, that stuff tends to hurt. It doesn’t matter if you’re a lust-filled toyboy or a fun-focused cougar, no-one’s truly immune. 

So we can end up feeling overly self-conscious; the whole ‘Oh God, what will they think of me??’ thing. And who wants to spend an evening with someone more concerned with themselves than they are with you? Exactly.

The easiest way to lift those self-conscious blues is to shift your focus. Studies show that people love and remember how someone makes them feel. Focus on helping your date feel relaxed, feel special, feel funny or interesting, and see how they blossom.


Share your inner world

Normal, as Whoopi Goldberg once quipped, is a merely a cycle on a washing machine. Everyone has a weird inner world. Everyone.

For someone to feel they know you better, give them a glimpse into yours; chances are, they’ll do the same. How do you do that? Discover their guilty pleasures. Or the geekiest thing about them. Ask something more interesting than the usual stuff about work, location and family. Be prepared to give your answers first, subtly showing how confident you are, to boot.


Make an appropriate effort

Yeah, we were all told not to judge a book by its cover. But let’s face it, this is internet dating. It was the cover that made you stop in the first place.

The way you present yourself on a date is a mark of respect, both for the person you’re meeting and for yourself. If in doubt of the dress code, google the place you’re meeting at (ladies, it’s not always going to be cocktail hour, ok?)

Making an appropriate effort as a toyboy really means being a gentleman. As this young guy in the den of two powerful cougars notes, it’s really hard to impress a woman these days.

A guy who’s confident enough to be a gentleman sticks out, in a good way. It means being respectful, attentive and masculine; offering the outward-looking seat in a restaurant (you’re giving her your undivided attention, and want the rest of the world to see her), pouring her water first, opening doors (including car doors), offering to carry something.

A younger woman may be too insecure to accept this behaviour, for fear of feeling patronised or beholden to you; an older woman is secure in the knowledge that she can do these things for herself, and so appreciates the consideration. That’s why you’re dating someone her age, yeah?

As for who pays for a first date; it can be a mine-field and there are no set-in-stone rules. Be wary of making assumptions, though. Focus on how you’d like your date to feel and remember, if they’re kind enough to pay this time, you can always find a way to return the gesture the next (and if there’s not going to be a next, absolutely insist on going Dutch!)


Of course, sometimes things don’t go to plan. You have a laundry melt-down and the only clean things you have to wear are sweatpants and a comedy t-shirt. You share your inner world and get called ‘Rain Man’. You talk, in detail, about custody problems with your ex. There are times when you mess things up, forget the rules and yet still get that second date.

It’s called ‘meeting the right person’. And no amount of lessons or preparation can guarantee that.

This post was written by a Toyboy Warehouse Community member.

So what do you think? What are your best insights and tips for a great first date?

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