My sister messaged me earlier today. She had been asked on a date and was panicking.
‘What do I wear?’ ‘What do I say?’ ‘What do I do?’ The questions poured out in a frantic monologue, possibly exacerbated by the fact the date is tomorrow. She only has one day to take action on any recommendations I might give her.
In my first year at uni I had a similar meltdown. There was a guy I liked. He asked me out on an actual date. I had no idea what to do. I had a full week to panic about it and I honestly don’t know if that was better or worse. I had no big sister to ask for advice and most of my friends couldn’t offer much insight either. I was more experienced than pretty much all of them. So how did I not know how to date? I had been in a two year relationship. I had tonnes of male friends. But to be asked out on a date, that stilted boy-opposite-girl-across-a-cafe-table when the boy was someone I barely knew? That was uncharted territory for me and it was terrifying.
While practice doesn’t necessarily make perfect with dating, it can definitely help. And I’ve been on a fair few dates since then. I still get butterflies every time I go out on a first date but I am more confident in who I am, and why I’m there. Sometimes my experiences of dating can even prove helpful to me, and to others.
So what did I tell her?
Wear what you are comfy in. Maybe not lounge clothes, but what you’d wear on a weekend, or in the pub with friends, or to uni. Something that’s you. After all, that’s who they asked to go on a date with, not some several inches of makeup, even more inches of heel, and a dress that would make Casanova blush. Even if you go somewhere uber fancy (in which case he should definitely give you a heads up so you can dress appropriately) a date is about getting to know one another. Several inches of makeup and a rule book don’t exactly lend themselves to authenticity and spontaneity, and they’d definitely jar with chemistry.
There is nothing wrong with wanting to impress, with making an effort. It’s flattering when someone you’re on a date with has made an effort, because they did it for you. That’s great, and you can definitely make an effort, but the effort should be – if anything – to enhance, not to disguise. If your eyes are your best feature and you want to showcase them, whip out the eyeliner. Add a bit of jewellery or a statement scarf. If it’s a pull-out-all-the-stops kind of place then go for it, but retain something that is you. A friendship bracelet you never take off, even if it looks weird with your cocktail dress, quirky tie of cufflinks you love – Harry Potter’s scar, Lego men, Star Wars, Minoan fertility figures, anything – even if they aren’t the traditional accompaniment for black tie. Besides, they’ll start a conversation.
The other thing is that if you’re wearing clothes your comfortable in, you stand a much better chance of being able to relax and actually enjoy your date. If your feet start hurting, your tie is strangling you or the under-wiring on your high tech stick on bra is digging in, it’s going to distract you and negatively impact your night. If miraculously they don’t manage to distract you from the awesomeness of your date then you might have found a keeper…
As for what you should say and do, that depends on you. Let the conversation flow. Don’t bring flash cards. If the conversation doesn’t flow then think if there’s anything in your previous communication (whether you met them on Tinder or at work) that can spark a new conversation. Still nothing? What about your surroundings? Try to pick somewhere to meet with lots of talking points- the food, the atmosphere, the tourists, the view…
Personally, I try to follow these rules. Firstly the less well I know someone, the more interesting the setting has to be. Go to a zoo, a museum, on a walk. If the conversation just flows that’s great, but if not, there’s plenty around you to comment on. If it’s going really well you could relocate to a cafe or bar perhaps.
Secondly, especially if I have never met someone before, but just a good first date rule, don’t commit to dinner. If you meet and decide you really really don’t get on, then there is little more excruciating than sitting through a two or three course meal opposite someone when there is a total lack of interest (not to mention the soft sobs of your bank account as it counts dating funds wasted on something utterly unsuccessful.) In fairness, wven without chemistry some kind of semi-civil conversation should be possible, but it’s still not where either of you would want to be.
So instead of dinner, opt for drinks. If it goes well you can propose dinner. Better yet, meet for coffee earlier in the day. Like drinks coffee can last as little or as long as you like, and while there’s (usually) no Dutch courage, there’s also no expectation that you’ll sleep together at the end of the date. But my personal favourite date? Brunch. Only, unless I’m sure I enjoy your company so probably not until the second date at least, you don’t get brunch because I don’t want my brunches marred in any way.
As for what you do, like what you wear and what you say, make it natural. If the date goes well, and the moment comes, and a kiss hangs in the balance and you want to kiss them then go for it. If it’s hanging there anyway, it’s probably like a game of chicken, and if you’re both chickens then sucks to be you. No guts, no kiss. If you both want to take it further than a kiss then go for it. Forget third date nonsense and milestones. Take it at the pace you are comfortable with. If you really enjoyed the date but don’t feel ready to kiss then that’s fine too. If you really enjoyed the date but don’t feel there’s any chemistry, also fine. Can be a blow, but often a lack of chemistry is experienced by both, and if neither of you is willing to voice it, then you slowly ghost one another rather than giving a friendship a chance.
So back to my sister, she’s going on a date on a beach, with a guy she knows from work. (I hope) she’ll dress comfy, paddle and be silly but most importantly herself, and have a fabulous time. And I totally expect a play-by-play after. Isn’t that what big sisters are for?
So what did I wear on my last first date? Jeans, top, leather jacket, ankle boots, and a touch of foundation because I had a few zits.
Where did we go? A museum and then a cafe because we figured we could handle sitting across a table from each other.
What did we talk about? Anything. Everything. The pieces in the museum, the weather, our studies, our families, ice cream flavours, TV tastes, feminism, our loathing of slow-walking pedestrians…there’s really no right or wrong, just see where the conversation takes you.
My best first date ever? A brunch date that lasted 6 hours and only ended because I had to start a waitressing shift, but he walked me all the way there. Yes, I took a risk on the brunch thing, but after our tinder conversations which had lasted pretty intensely for several days I was sure we’d at least have things to talk about even if there was no chemistry (there totally was).
The one thing I cannot stress enough is never expect your date to end in sex, or even in a steamy make out sesh. And definitely don’t look disappointed when you discover it’s not on the menu. Particularly if you have made not the slightest attempt to get cosy all evening and then as soon as we leave the bar you seem shocked I don’t intend to go back to yours. You haven’t even tried to kiss me, or I haven’t tried to kiss you. Either way, kissing a pretty good indicator of how things might pan out, so maybe start with that? But also, dating is about so much more than sex, and if you make it your end game then that’s fine, but you’re not the date for me.