I’m a Match-Maker, Here are the Essential Need-to-Knows for a First Date in 2024

With Valentine’s Day approaching, we teamed up with thortful and exclusively interviewed match-making expert and owner of award-winning dating agency Cupid In The City, Siobhan Copland, to discuss first date etiquette in 2024.

To discover why coffee shops and restaurants are the worst places to meet, the exact way of resolving the awkward bill payment at the end of a date, how to handle a catfisher, the foods you shouldn’t eat, the best way to settle pre-date nerves and more, the interview below is the perfect source of information for new daters and singletons meeting on Valentine’s Day. 

What are the best and worst dating locations for a first date?

“I personally don’t like coffee dates, I find them a little too formal, and coffee shops are often overcrowded, so it feels uncomfortable to be meeting someone for the first time, queuing up for 10 minutes to get a hot drink, and then you may not even get a seat!

I’d recommend picking an actual venue rather than meeting at a tube station. Unless you are planning to stand by a clock tower with flowers, it is totally unromantic and stressful to be looking for someone in a busy crowd, to then wander around hoping to find somewhere.

It really is the thought that counts, so think ahead to where will be comfortable, warm, relaxed, and ideally book in advance to ensure you have seats waiting. I am quite fond of activity-based dates too, a couple I recently set up went to a glow-in-the-dark arts class for example.

It gives you a focal point of discussion and helps you to be present, and not go into interview mode of asking a bunch of questions which can be quite intense, so I think, particularly if you are someone who gets quite nervous on dates,  a dinner date will increase your nervousness and intensity, so I would suggest an activity which you can focus on, and focus on the fun.

Dinner, I suggest, for when you are more comfortable, but ensure there is the option to get a nibble, hunger can change our moods quite significantly.”

Which foods should you avoid eating?

“Anything with a lot of garlic and onions. Just in case you do go in for a kiss, and before you order nuts or shellfish, check your date doesn’t have any allergies. I’d also recommend not eating anything that puts you at risk of making a mess, such as spaghetti and soups.

No one really wants to hear slurping on a first date meal and avoid foods like ribs where you might get food stuck in your teeth. You don’t want your date to have to tell you about the spinach that’s been sitting in the front of your mouth after ten minutes of conversation, as let’s face it, they will be thinking less about what you are talking about and more about how to tell you.

How should you approach someone if you aren’t sure, it’s them?

“I would always try to get their number first or offer yours so you can text or call when they have arrived. But I would also message them first if they don’t feel comfortable giving their number to say you will be at a landmark, say for example, waiting outside the red phone box wearing a navy shirt.

I also always suggest smiling first if you think it is them, you can usually tell by the way someone smiles back whether they are really taken aback, there is usually some eye contact that suggests some recognition, and a nod.

So, look out for body language, and if you can’t see them after a few minutes, position yourself somewhere away from crowds and send a message describing where you are and what you are wearing.”

How should you react if you’ve been catfished?

“With catfishes, they rarely want to meet in person, or at least say they do but come up with a bunch of excuses because they really relish the attention they get from their online persona.

But if someone shows up looking nothing like their photos, I would be very upfront and say, ‘I am sorry but I am not comfortable continuing with this date as I was led to believe I was meeting someone else – you aren’t the same person from the photographs and dishonesty is a total deal breaker’, and leave.”

How should you greet a person on a first date? Is it polite to kiss on the cheek or is that overwhelming someone’s personal space?

“I think for the first interaction I would avoid such close physical contact, if at the end of the night you are at ease with each other, you may want to end with a kiss on the cheek.

Read their body language and how close they have been towards you throughout the night. Are they making strong eye contact, do they lean towards you? At the start though, a smile eye contact and an upbeat ‘hi nice to meet you’ will do fine!”

How can you settle any pre-date nerves? 

If you have time, a little workout and shower could work to ease some tension, try not to have caffeine before as it can make you jittery. Get there before your date so you have time to get seated and relaxed, say 15 mins before, and stick on some music or read a book till they arrive; best to look occupied rather than nervously looking around.

Which topics should you avoid talking about?

“Exes, anything that also makes you appear that you are of a negative mindset like complaining about your job, complaining about poor treatment from others. Try to keep things light and fun to boost your chances of a second date.”

What are the worst things you could say on a first date?

“I think it is not necessary to ask questions like why are you single or how long have you been single? Stick to feel-good topics – opening up someone’s relationship profile could make them upset – they could have recently come out of a tough break up and it’s taken them a lot of courage to start dating again. Also, definitely avoid politics, having different opinions could end up in complete disaster.”

How can you show you’re interested without being too keen?

It has to feel reciprocated, so I think put it out there that you would like to meet again and gauge their response. If they seem pleased, try to book a second date on the first date by checking each other’s availability the following week.

Once a week for early dating in the first month is about right, and not lots of texting in between. You could even make it clear you are not big on texting when you are first getting to know someone, you prefer to get to know each other when you are face to face.”

Should you bring a gift to a first date? How much should you spend?

“This is the only time I can agree on your presence being the present for the first date, gifts are something to work towards and have more of an impact once an emotional connection has been built. Plus, overspending or a gesture that’s too big could scare your date, and you don’t want to make them feel bad if they’ve brought nothing for you!”

What is the etiquette for splitting a bill, who should and shouldn’t pay?

“I think the etiquette is that whoever invited the person there should really pay for the first time, and after 2 or 3 dates I think it is polite to suggest splitting or to make it your treat.”

How can you avoid awkward conversations about paying or not paying it?  

“When the bill comes, I think it is always polite to ask. It doesn’t matter who says it first, but I would always approach with “How would you like us to handle the bill?” If one person insists that they will get it, then respond graciously and thank them for their generosity and kindness, that is enough. You don’t need to then say, ‘ok I will get the next one.’ It’s not about owing, it is about accepting someone wanting to court you effectively.

If they suggest splitting, then you go with that. Always be prepared to pay, but if the person wants to treat you, let them, don’t make a fuss. Don’t instantly assume you’re getting a free meal though, it will leave you annoyed if the other person wants to split it. And finally, a big red flag – don’t bring the bill up at the start of the date, don’t instantly say “We’re splitting this, aren’t we?”, or “You’re paying, aren’t you?”, as it will instantly make things feel awkward.”

How do you politely decline if you aren’t interested without being rude?

You have to be honest in this situation, rather than saying yes to a second date and ghosting them over texts. Something along the lines of ‘I have really enjoyed meeting you and had a lovely time, but I just don’t feel there is that connection between us that I am looking for. But I would happily see you again as a friend sometime’ would work well.”

What are the best and worst ways to leave early? 

I would always stay at least an hour, any less does seem rude unless you have been catfished. The best way is to simply ensure the bill is settled and give your reasons for needing to leave, you could even be honest enough to say at that point, ‘I don’t feel there is the connection I am looking for’, but always wish them well and never sneak out.”

Anabel Cooper

Anabel is a graduate of King’s College London and upon graduating, she set out on a journey to inspire and empower women through her words. Besides working as a digital marketing expert, Anabel is a freelance copywriter.