Posted inRelationships

‘Should I Stay, or Should I Go?’: A Beginner’s Guide to the First Date

Aaron James, (self-confessed) relationship aficionado, reveals his top tips for the first date. Fear not, you won’t find the cliché ‘be yourself’ here. Illustration by Grace Kirman.


You’ve matched on Tinder and things seem to be going in the right direction. You’re into the same music, you like the same shows, and they even understand your erratic sense of humour. Everything feels right – natural, even. The next step? Arrange the first date. 

My first piece of advice: if it feels natural, then you’re probably onto a good thing. Trust your instincts and follow what feels right, as this means you will enter the date with the right energy. If you think that a relationship with this person is unlikely, don’t lead them on to a romantic date.

Ask your prospective partner out in a chilled, informal way: ‘Fancy going out for coffee some time?’ may seem vague but it relieves pressure from what may be a nervous situation. Phrases like ‘some time’ or ‘when you’re free’ strike a good balance between being keen and smooth, since they allow the other person to accept or decline. The last thing you want is to make your partner feel like they can’t say no. 

Opening phrases such as:  ‘Would you like to get a coffee on Thursday afternoon?’ feel suffocating and could harm your chances. I recommend splitting your date arrangement into two steps: broad organisation (so that you know your partner wants a date) and then fine-tuning (sorting out the day, time, and location). 


Success! They said yes and the rush of butterflies has begun to abate. It’s now time to arrange the date.  

The details you’ll need to make clear are day, time, and location. Seeing as you asked your partner out, it’s more than likely this will be your responsibility. I advise that you suggest a day and time which are unlikely to cause a clash. Few people will want to go on a date at 9am in the week and even the most eager daters have tutorials and classes to attend. I always find that evenings are much better and arrange the majority of my dates between seven and eight o’clock. If your date has mentioned a looming deadline or essay hand-in, suggest that you take them out to celebrate their hard work. This shows that you have listened to your partner and are keen not to overload their schedule. Two words: brownie points.  

Planning a location/activity can often be stressful as you’ll want to find a good balance between formality, atmosphere and, of course, price. One of my favourite date ideas is to enjoy some coffee and cake in Christ Church Meadow. It’s romantic and extremely easy to organise. Take your date to your favourite High Street coffee shop (so that your drinks are still hot when you reach the meadow!) and find a spot by the river. If you’re eager to impress, you’re spoiled for choice for restaurants and bars across Oxford.


Even with your date arranged and sorted, you’re bound to be nervous – and it’s a good sign if you are. A healthy level of nerves shows that you want the date to go well. However, if you find that you’re anxious, fall back on your support network for guidance. Ask for friends’ opinions on your outfit choice and conversation starters. Dating should be a positive experience and your friends will be happy to help you. 

With regards to clothing, try to strike a balance between comfortable clothing and something which flatters. Tracksuits (unless on a sports-related date) are a no-go in my book. Remember to brush your teeth and spray some fragrance – small details like this will only make the date a more positive experience. 

Don’t keep your date waiting. It’s not cool. Get to the arranged place early and even send a text when you’re on your way. A quick message can put your date’s mind at rest and let them know that you’re not about to stand them up. Remember, they may be just as nervous as you are. 

Once on your date, just relax. Conversation starters like college life and weekend plans may be classed as small talk but these topics often lead elsewhere. Finding some common interests will soon link you to funny stories and interesting anecdotes. Start off with Netflix shows and music tastes. Feeling extra flirtatious? Suggest that you travel together some time and indicate that you’re serious about the date. 

The age-old question of who pays for a date is tricky. Generally, I always think that the person who decides where to go should pay. It seems unfair to ‘take’ someone to an expensive restaurant and then expect them to pay. I usually foot the first bill and then suggest that my date gets the next. Although this may seem daring, it lets your date know that you’re interested in seeing more of them in a cheekily flirtatious way. 

If this is not the case, casually suggest that you ‘go Dutch’ (and split the bill in half). 

Courtesy and good manners should always be at the front of your mind. Always offer to walk your date back to their college/accommodation, especially if it’s dark, but never expect to be welcomed back into their room. Boundaries are important at any stage of a relationship.


I usually walk a date back to their place and then let them know when I am home safe. This opens a good opportunity to thank them for their company and to let them know if you’d like to go out again. You may be eager to know which ‘second date signals’ you should look out for. However, such indicators can be misleading and unreliable. It is much more mature to be upfront and ask whether a second outing is on the horizon. Be sure to respect your date’s response, whatever it is. 

Not every date will end in marriage and even my recommendations in this article are not entirely foolproof. But the worst that can come from of a first date is a nice evening out and the possibility of a good friend – and that’s not too bad, right?