How To Tackle Valentine’s Day When You’re Only Two Dates In

January is the best time of the year to be single and swiping, hands down. The endless string of glowing faces in your match queue and long, balmy nights make squeezing in back-to-back dates a breeze.

But just as you’re easing into a comfortable rhythm with one stand out bird come the end of the January, there lies a sneaky kink in the road ahead set to derail your sparkling new summer romance. February 14th.

Valentine’s Day is the ultimate relationship accelerator

Valentine’s Day is incompatible with everyone out there actually looking for love; singles on dating apps. Because going in too hard (or not hard enough) can completely thwart the chances of finding it.

Suddenly, your carefree string of casual dates with one or multiple birds has to be defined: Are we even exclusive? How much is this going to cost me? Should I go off-grid for the week?



Sadly fellas, the way Valentine’s Day is sold to us means that you bear the brunt of it. But we’re here to help you navigate the heart-shaped land mine come mid-February and find that Goldilocks sweet spot to celebrate the day when you’re just two dates in.

How soon is too soon?

There is no golden ratio. Every relationship has a different timeline, made even murkier by the endless ways to connect and date virtually before meeting up for a date in person. Have you just been messaging on the app? Did you video call first? How long has it been since converting from a dating app to text?

Keep it simple and go with your gut feeling. If it’s very early days but you really enjoy her company, the banter is great, and you are curious to see where it goes; then definitely feel confident to drop the Valentine’s Day hint. Perhaps even spin the day into a laughable, tongue-in-cheek joke. Ignoring the date altogether is a sure-fire way to look like a dickhead, so pick an approach and stick to it.

Read the room

Everyone has different expectations of Valentine’s Day, including some who have been seriously burned by it in the past. February 14th is notorious for making people question their own commitment and baggage, and has been a make or break for many since the dawn of the holiday.

The best workaround is to gage her vibe and establish how she feels before making any assumptions. Lead with a touch of humour and a sprinkle of sarcasm, when you drop something into the chat like, “So Valentine’s Day is coming up, and you a take it or leave it kind of girl?”

You can even drop it into your Bumble chat as a question prompt you both need to answer. Then, when you get a response, actually listen. Women appreciate you listening to them, above all else.

V-day can be a great reality check

Singles act “chill” in the first stages of dating, but deep down we all want to vibe with our new match and have our feelings of excitement validated. Even if you’re only a few dates in.

Any bird would be stoked for you to bring up Valentine’s Day. It’s effectively a subliminal, “Hey, I like you and want to spend more time with you.” And that is a rare, yet very welcome thing to hear in the stoic world of swiping.



Hard chats, especially in the early days, provide good insight into each others values and maturity levels. If it scares her off, it’s likely all on her and nothing to do with you. Equally, if she’s overly keen to use Valentine’s Day to flaunt your very undercooked relationship on her Instagram grid to the world, maybe she’s not the right one for you. Consider it a favour.

You’ve got a V-day greenlight, now what?

It’s a huge gamble to suddenly drop a $1k chip on black if you’ve been putting down fivers all night. Match your efforts on V-day with the exact same momentum and pacing your dates have taken to date. If your previous date was…

  • Grabbing a quick coffee: lock yourself in for a long late lunch.
  • Sending her home in an Uber after getting it done: encourage her to stick around and plan a nice breaky or morning activity.

Treat it as any standard level up from one date to the next. But you can throw in a few extras to denote that Valentine’s Day spirit; like a surprise round of cocktails sent to the table, or shooting off a cute text the morning after.

Valentine’s Day date ideas

The calendar gods are in our favour this year. Valentine’s Day falls on a Sunday, allowing you to go in as easy or as hard as you like.

A strategic and seemingly disguised Saturday night dinner on the 13th can effortlessly flow into a midnight toast for Valentine’s Day. If you brave the 14th, tack a round of margaritas onto Sunday brunch, or settle in for a cosy late lunch.

The most difficult part of dining out is landing a reservation that doesn’t cost an arm and a leg or surround you with other couples flexing for the rights of ‘best couple on ground’. No doubt venue capacity limits will exacerbate things this year.

Luckily the pandemic that shall not be named has normalised and made incredibly foolproof the concept of cosy dining at home for date nights. Organising an at-home cocktail making set up, or pre-ordering a bougie dinner delivery can be a lot more romantic, hands-on and intimate than dining out.

Just remember, hosting is not a get out of jail free card. You still have to have made a concerted effort, and ensure your place is tidy and up to scratch.

To gift or not to gift?

It will be a rocky start if you’ve wrapped up the latest Apple Watch when she comes empty-handed (true story). And you can bet that you and your gift will be dissected at length in her girl’s group chat. You’ll wish you had saved your pennies for Bumble Premium instead because it’ll be back on the app for you come February 15.



It’s much safer gameplay to funnel your effort, and cash, into an experience you can share; like flicking straight to that coveted back page of the wine list over dinner giving zero fucks if the waiter picks out a $60 or $200 bottle of vino.

Just have a plan, literally any plan at all

Above all else, having any activity or venue booking that oozes some semblance of effort on your part is the way to smooth sailing through February 14. On the flip side, if the worst should occur, the surge of users on dating apps in the lead up to (and especially the day after) Valentine’s Day is real.

So if you’re yet to meet some solid contenders, jump on the app and start swiping. Just make sure your photos are fresh, you’ve had a good crack at filling your entire profile and syncing your Instagram. It’s is always much appreciated.