You “swiped right” (assuming you’ve been messaging each other for a few days and she didn’t go silent when you tested her sense of humour with a cringe-worthy pun.
Perhaps she’s the one for you – or perhaps she’s actually a lonely old bloke from Hull. But, either way, the only way to find out is by asking her on a date. Digital flirting and that perfectly posed profile picture of you balancing a kitten and a puppy in either hand after an intense workout won’t count for anything unless you can charm in person.
Unfortunately, charm is hard to teach (although you may have honed your skills over the years) and we can’t tell you what amusing anecdotes to share or what questions to ask. What not to ask, however, is much easier.
1. Do you think I’m attractive?
First impressions are important but, just because what to wear and how to style your hair been bugging you ever since you agreed a time and place, you have to leave all worries about your physical appearance at the door. Tell her she looks good without being creepy, and don’t worry if she doesn’t return the compliment – if she wants to see you again, assume she was happy with how you look.
2. What are your strengths and weaknesses?
Avoid asking any formal questions and that includes asking her to bring an up-to-date CV – this is not a job interview. Do not shake her hand and ask her to “take a seat” and, most importantly, do not quiz her on salary expectations.
3. What music are you into?
Everyone dreads this question. Unless it’s a real deal-maker or breaker for you it’s probably a good idea to avoid talking about music at all. While it might help you find common ground it could also be quite divisive. So unless she’s wearing a band t-shirt, which could help kickstart such a topic, it is probably safer to assume she likes “a little bit of everything” and put that subject on ice until you get to know one another a bit better.
4. Do you want to get the next round?
If you’ve paid for the first set of drinks, you may be hoping/expecting her to pick up the next one – but try to refrain from actually asking. If she was already planning on reaching into her wallet, you will offend her. And if she wasn’t, you’ll embarrass her. Try to relax and not let that become “a test”.
5. Who was that guy I saw you with on your Facebook page?
You’ll be forgiven for checking out your date’s profile picture, but try to avoid thinking too much about the photo of her with an ex-boyfriend underneath the Eiffel Tower three years ago. Never, ever ask her about it. Live in the now and don’t be a stalker.
6. Do you work out?
It’s fair enough to ask her about her about her hobbies and interests. Do you play any sports? Do you like to go running? Just don’t phrase the question too aggressively as it may rub her the wrong way – especially if she’s not a total gym addict.
7. Can we take a couple selfie?
Selfies are for social media, first dates are not. Even if your date is the most attractive girl you’ve ever met and you’d like nothing more than for photos of your smug face next to her beautiful one to go viral, posing for a selfie with you will probably make her feel uncomfortable. Remember also, if date two never happens, that selfie will always serve as a painful reminder of how less than perfect your dating skills might be.
8. Do you want to go to Paris?
Get off SkyScanner and calm down. You might have had a great evening together and you might think that she’s the type of girl who’ll be won over by clichéd romantic gestures, but don’t ask her to commit to going away with you just yet. If you want to impress her, by all means, plan your next date at a nice restaurant. You can even break out the Michelin Guide, if you’re feeling ambitious. But keep it local – at least until after your first sleepover.
9. Have you ever cheated on a boyfriend?
Relationship crimes are rarely one-sided. If she has been unfaithful to a former boyfriend (or been cheated on), there’s likely to be a story behind it and it’s probably not a happy one. Let’s keep things upbeat, shall we? Airing this sort of dirty laundry should be saved for date number 10 or beyond.
10. Do you want to see me again?
You’ll probably be able to gauge whether or not you’ll be seeing each other again after a few hours of interaction. But, even if you need a little more assurance that you’ve been sufficiently charming, don’t ask this question. You’ll come across as needy and she’ll feel forced into saying yes. Leave it at “I had a great time” or “I really enjoyed this evening”, and get in touch later on in the week with a proposed time and place for the second date.