Do’s and Don’ts of a Valentine’s Day First Date


If you've asked a girl out on a first date on Valentine's Day, then kudos to you, good sir – you have inexplicably doubled the amount of pressure a first date usually places on a man's shoulders by holding it on the most romantic day of the year.

In doing so, you're likely going to need a few tips to ensure that you make it through February 14th with your dignity in tact. Luckily, we here at Crave Online have compiled a list of Do's and Don'ts that should see you through the date.

DO: Make a big deal out of your spontaneity.

Valentine’s Day is usually a date reserved for existing couples, not for two people who have only recently met. This is why you need to assure your date for the evening that you do not make a habit of going on first dates on Valentine’s Day, but rather it was something that you decided to do in this one specific instance because you are spontaneous and mad and any other quirky personality trait that women seem to go for.


DON’T: Make yourself seem desperate.

If you’ve asked out a girl you don’t really know on Valentine’s Day, then she likely had one of two reactions:

  1. She thought it was really sweet.
  2. She thought it was kind of weird and desperate, but decided to give you a chance anyway because you might have just been trying to be sweet.

As previously mentioned, Valentine’s Day is usually enjoyed by couples who have spent weeks/months/years together, so if you let her think that your decision to ask her out on this day was anything other than you being cool and spontaneous, she’ll likely think that you’re planning to buy her one too many drinks and take her to a drive-thru wedding chapel.


DO: Go somewhere casual.

Bars are your friends on Valentine’s Day, because the only people inhabiting them are going to be fellow singletons who actually don’t have dates, therefore making you 110% better than them.


DON’T: Go to a restaurant.

All restaurants on Valentine’s Day are going to be packed to the rafters with men and women swooning over one another, so taking a first date out for a meal will likely lead to you looking like a deer caught in headlights, unsure of how to conversate with her when you’re surrounded by people who will definitely be having sex later on.


DO: Get her a gift.

Just because you don’t really know each other doesn’t mean that you should completely ignore the fact that it’s Valentine’s Day. Don’t go overboard with the gift-giving – a huge bouquet of flowers will not look good whilst awkwardly positioned on the bar – but a box of chocolates or something equally cliché will do the trick.


DON’T: Buy her a card.

Cards are solely reserved for partners, friends and family. Buying her a Valentine’s Day card will likely creep her out, as there are no cards designed to be given to someone on a Valentine’s Day first date – unless you find one with a message on it that reads “To the immensely creeped out girl sitting opposite me in this bar, who is wondering whether or not I think that we’re now an item because I asked her to go on one date with me and now I’ve bought her a card like we’re f***ing engaged or something”.


DO: Capitalize on the special day.

It's Valentine's Day, so assuming that the date went well and you didn't vomit on her shoes out of nervousness or anything, then this is the point where you can likely capitalize on the fact that you're both together on the Most Romantic Day of the Year and go in for a kiss. Obviously, you still have to read some signs here to know whether or not you're going to be awkwardly rejected when you do, so don't come crying to us if you wind up being publicly humiliated/pepper sprayed.

DON'T: Go overboard.

Love is in the air, but it definitely won't be in your future if you find yourself becoming too swept up in the Valentine's Day spirit, have one too many drinks and decide to pledge your undying love to her.
Header Image: Getty Images