How To Go on a Date

I’ve been on a lot of dates. Mostly first dates, to be honest.

Some have been good, some not so good (read: bad). But, we persist! Thankfully, we’re no longer limited to going on masked, socially distanced walks (unless that’s what you’re into), and dimly lit wine bars are back on the table. And, although not every rendezvous will be fireworks and delicious sexual tension, sometimes it’s just nice to meet new people. IMO, going on dates is always fun because even when they’re a bit terrible, they usually make for a good story. But, there are certainly ways to avoid potential disaster.

Be prepared
If you’re the one doing the asking out, have a game plan. There is nothing in this world that makes me less enthusiastic about a date than an obvious lack of forethought. It doesn’t even have to be a good plan. A bottle of wine in the park counts. Suggest a specific pub. Make a booking somewhere. You can ask for input, but offer up some options—it’ll show you’ve thought about it and you give a shit. If all else fails, bowling is a great first date. Teppanyaki is not (it totally is—ed).

Ask lots of questions. Seems obvious, maybe, but it’s harder than you’d think. It is not a job interview, but it’s nice to be interested in the person you’re courting, and if you’re not interested in them, why are you even bothering? Engage with their answers, too. I know that I am absolutely terrible at not interrupting when I get excited, but I have learned to stfu more and let people talk about themselves. Besides, there’s nothing sexier than watching someone’s eyes twinkle while they talk about something they’re deeply passionate about.

Be yourself
At work, I help a lot of people choose wine for first dates (or third dates, etc.), and they always agonise over the ‘right’ wine to take. I want you to know that the right wine is whatever the fuck you like. It’s an opportunity for the other person to get a sense of who you are, and what you enjoy. Besides, if they don’t like it, that’s okay. If we all liked all the same things all the time it would be very, very boring. I’d much rather try something new that makes someone excited and happy. Basically, don’t be inauthentic, it’s a waste of everyone’s time and it’s boring. If they don’t like you for you, file it under ‘N’ for ‘Next’ and move on.

Cheque this out
Who pays? This is a question with no right answer, but I do have some thoughts. Money stuff can be awkward but it’s a good opportunity to test communication (which is the most important part of any relationship). If it’s a first date, keep it simple: go for a casual drink and offer to buy a round, or make it clear if you’d like to pay. Splitting the bill is pretty standard and I’m all about equality but equity counts here, too. Sometimes ‘splitting’ the bill can mean that one person pays and the other one pays the tip. Also the phrase ‘I got it’ is pretty hot. If you want to see them again, suggest they get the next one. That seems fair and opens up the conversation for locking in another date.

Going in for the pash
Read the room here. The end-of-date smooch is never a sure thing, but if all signs point to yes, obviously you should go for it. If you’re not sure, ask. ‘Can I kiss you?’ is an easy and sexy way to make sure everyone is on the same page about making out and, honestly, the worst that can happen is a ‘No’. It might be awkward for a moment but is usually far less awkward than an unwanted kiss. Anyway, communication is sometimes non-verbal. If they’re attempting to shake your hand goodbye, they don’t want to touch tongues. If you do get the green light, godspeed.

It’s okay if it’s not a vibe
Sometimes it’s just not. Doesn’t mean anything other than you’re not compatible or you want different things, and that’s fine. It’s okay to leave a date early. If you’re not having a good time, chances are the person you’re with isn’t, either. I’m not advocating downing your drink in one and making a run for it without paying (unless you’re feeling unsafe and then yes, bail) I mean just gently wrap it up and be on your merry way. Life is too short to entertain things that are not fun, exciting or enjoyable.

Mutual ghosting
I once went on a date that was an absolute fizzer. That’s fine, it happens. Shortly after we parted, I got a message detailing why I would not be an ideal girlfriend. This was well-intentioned (maybe), but it probably would have been the ideal time to employ the ‘mutual ghost’ – where both parties leave the date without making any allusions to seeing each other again. That said, it’s fine to not follow up, and not awkward if you do bump into each other (it happens). Unfortunately, this doesn’t always work and sometimes you have to duck behind the potatoes at Harris Farm.

One last thing: being ghosted can be awful (rejection hurts), so if you are in a situation where someone is obviously keen and you’re not, a short but kind text is often appropriate.

Happy dating!


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