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The Awkward Man’s Guide To Asking Out A Woman You Already Know

“If your attempt goes well – great! But if it does not – awkward (for both of you).”

You’d think it would make it easier, but asking out someone you already know (or kind of know) is actually more fraught than hitting on a stranger.

Matching with your barista on bumble, for instance, is like running into a friend with an identical late-night Mc Donald’s soft-serve: it’s not the sexiest way to be spotted, but you’re both clearly thirsty. Matching with (or asking out) a stranger is stressful enough. But when it’s someone you are guaranteed to run into, the stakes are even higher.

What if they didn’t realise it was you when they swiped? What if they swiped ironically? What if they’re actually into you? Random thoughts turn to elaborate scenarios: “Can we casually hook up, or do I have to start a relationship with them?” Of course: the simplest solution is to just remain friends.

However, if you actually want to try and hook up with your barista (or a non-close friend) we’d recommend arming yourself with our tried and tested advice; a) to maximise your chances, and b) to minimise any potential awkwardness. And tread carefully, because—as one Reddit thread recently revealed—the consequences can be quite inconvenient…

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Not only might you have to find a new cafe (if things get ugly), but, as one unfortunate dater found out—your crush might have only swiped right in a sort of friendly, mutual acknowledgment, only to be highly confused when you reveal you’ve been lusting after them for months… Or if you’re asking them out in real life, they might just… well… say no.

Suffice to say: as well as helping you work out exactly where you stand, your opening line needs to go down as smooth as a Macadamia Macchiatto. If you find this tricky: we’ve compiled a list of tips for you.

Panic

When your phone first informs you that your bearded crush (or tattooed crush-ette) is interested in more than just your bizarre taste in caffeine, you should take a second to panic. While this may seem counter intuitive to generating a solid plan, taking a moment to absorb the gravity of the situation will help you come up with a realistic strategy.

Make Up Your Mind

Unlike matching with a stranger, you can’t just ignore or block your barista (or casual acquaintance) if you change your mind on seeing them once you’ve already matched or asked them out. So make sure you’re attracted to them. Are you willing to put your friendship at risk for the sake of a one night stand or (potentially) short lived relationship?

If not, it’s crucial that you defuse any sexual tension. Fast. If you’re on a dating app, try a light hearted joke like: “How many dick pics have you gotten so far, lol” (but make sure it comes off as a joke, not a pick up line). On the other hand, you are willing to give it a shot, we suggest you keep reading…

Think Of A Plan

If you are ready to add some ‘spice’ to your pumpkin latte, you need a plan of action. Are you going to play it cool, or take a leading role? Consider your interactions so far. Have they been flirty? Do they expect you to be flirty? Do they even know how to spell your name? Use this as your guide to picking an appropriate ice-breaker…

Come Up With Some Humorous Ice-Breakers

If you are looking for a balanced approach—not too strong, not too weak, “Come here often?” is a good choice. It starts the conversation, has a touch of humour about it, and is fairly straightforward (consider this the flat white of openers).

Other options are the “Monkey covering eyes emoji,” which is perfect for when you’re wanting to signal interest but still allow them to make the first move (the latte of openers) and, “I always had a mini crush on you”—for when you want to make your intentions perfectly clear, and get things moving as quickly as possible (the double espresso of openers).

Take It To The Next Level

If your ice-breaker goes well, casually suggest going out for a few beers. Or better yet: that they teach you their “coffee” skills. At your place. On the coffee machine you just oh-so-coincidentally bought.

Oh and for those of you that have a crush on your barista (or anyone you ‘sort of’ know), but haven’t matched with them on Bumble, we hit up Chris Manak, one of Melbourne’s leading dating coaches, for his top tips. This is what he had to say.

“Personally, I suggest to my clients to add them on Facebook in this situation. If she works in the same office building, or at the local café, or is the bar hostess of your regular, etc. these are examples of situations where if your attempt goes well – great! But if it does not – awkward (for both of you).”

And.

“If you’ve got the balls to go for it, well done you, but if you haven’t, just watch how she reacts when you find a reason to add her on Facebook. This reaction will tell you a lot, about her interest in you, and it will also open the door for a future chat and getting to know each other more.”

Happy swiping!

RELATED: Important Dating Rules You Need To Know Before Hooking Up In France 

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