Aaaah, Valentine’s Day. A seamless whirlwind of romance in theory, but in reality it can be a lot more awkies, with bills to pay and gifts to buy – or not. Don’t stumble your way through another February 14th, consult our dating directive below.


Serious relationship: Wrong. It’s up to you both to make each other feel special, so even if you’re on the receiving end of most of the wooing, get involved in the plans for the day, or prepare something sweet yourself. The day is not just about his love for you. It’s about your love for him too.

Just started dating: Wrong. Although you might want to be swept off your feet, he wants to feel like he is YOUR valentine too. So don’t just sit back and let him do all the hard work, plan something small too – and we do mean SMALL. If there’s one thing a guy hates, it’s someone trying to steal his thunder.


Serious relationship: It’s assumed that you’d spend the day together, but it’s still sweet to ask him to be your Valentine. Only have dinner plans? Don’t let the romance wait ‘til 8pm, wake him up with breakfast in bed or send him a sentimental card to set the mood for the day. Out with social media messaging and in with the old school romance.

Just started dating: Break the ice in the morning with a message that lets him know you’re excited for your date – you can’t go from zero to passionate love affair in under a minute.


Serious relationship: Each couple has their own agreed upon T&Cs when it comes to paying the bill, and Valentine’s Day is no exception. The one who organised the date should in theory pay for you both, but a courtesy offer (you know the one, that classic but insincere purse reach) shows you don’t take him for granted.

Just started dating: If you’re in a brand new relationship, the good news is he’s still on his best behaviour – meaning maximum chivalry and most likely a free meal. Lucky you!  If so, thank him gracefully and offer to pay next time. Or, if he’s taken you out a few times already, now is your time to jump in and insist you pay – it won’t go unrewarded.

Splitting the bill? The ultimate romance killer.


Serious relationship: It’s a good idea to discuss this with your partner before the day to avoid any nasty surprises or disappointments on either side. If he's the one arranging a romantic date, a thoughtful gift (like a MANBOX subscription) is a nice touch.

Just started dating: Because any good gift - especially a Valentine’s gift - should be personal, rather stick to an awesome date this year and keep the presents for when you know each other better. It’s also bound to be if you buy him a gift and he rocks up with nothing. Chocolates and flowers are a go. Colognes, picture frames and underwear - not so much.


Serious relationship: Yes, unless he totally forgot Valentine’s Day.

Just started dating: If you plan on seeing him again, then yes. After all if you give him the cheek on Valentine’s Day of all days, he’ll probably assume you aren’t interested. If you don’t plan on seeing him again, then no – not even if he paid for dinner. You don’t want to lead him on and you shouldn’t feel pressurised into it because you got a free overcooked steak and a glass of box wine.