How to Woo Your Woman with Strategic Spontaneity

How to Woo Your Woman with Strategic Spontaneity
Women love guys that are spontaneous. Problem: A lot of guys hate being spontaneous. The solution? Surprisingly simple and incredibly effective.

It’s no secret that plenty of women are looking for a man who is spontaneous, who can sweep them off their feet with an impromptu vacation, surprise gifts and spur-of-the-moment plans. It’s also no secret (at least going by all the romantic comedies based on it) that for most men, spontaneity doesn’t always come naturally or isn’t embraced happily, especially when it comes to romance. And for many, the effects spontaneity has on a schedule are downright shunned. These are stereotypes, sure, but like most stereotypes, they have a ring of truth about them.

It’s easy to paint spontaneous gestures as just one more romantic technique, a way to impress your partner and get yourself into their good books. But it’s also worth remembering that in any long-term relationship, a lack of spontaneity can be a death sentence. Every couple gets into habits, and habits can eventually become ruts. As your lives slip into a regular schedule, it’s easy to get bored, and the places and activities that used to excite you will seem rote and dull before long. If you’re bored by what you’re doing together, it’s only a matter of time before you get bored of each other’s company, period.

The problem is that if you’re not normally the spontaneous type, it can be a surprisingly hard skill to master. If you hate the thought of giving yourself less than two months’ notice to book a weekend trip, it won’t be easy to just run to the airport, hop on a flight and hope you can find a hotel when you get there. Odds are, before you get anywhere near your plane you’ll be obsessing over your work vacation days, your dry cleaning and whether or not you turned the heating off.

If the idea of being asked the day of to go see a hot air balloon show on a Saturday you thought you were going to get to relax fills your body with opposition, it won’t be easy to give up your one free afternoon.

If it’s something that your partner is looking for though, spontaneity can be one of the most powerful ways to romance them – they’re never likely to forget the time you grabbed them from the office at 5pm to whisk them off for a surprise weekend getaway. And let’s not forget, that spontaneous gesture will be all the more impressive and effective if it’s not how you usually behave.

It’s also worth remembering that for most Primer readers, now is the perfect time to be spontaneous, because you likely don’t have all the obligations tying you down that you might in a couple of years. If you have kids or pets down the road, it can be near impossible to get away without some serious planning, so take advantage of the freedom that you’ve got right now.

stra·te·gic spon·ta·ne·ity (n.)

The act of using a swift amount of advance research, preparation, or scheduling (for restaurants, date ideas, weekend trips, vacations, etc.) that’s presented in the moment as an exciting impromptu activity. Typically used to thrill significant others while mitigating the stress and headaches of actually being spontaneous.

Dates & Activities

It may sound contradictory, but the first and most important step in pulling off something spontaneous is a shred of planning. A small bit of consideration in advance can save a lot of work down the line, along with removing most of the possible headaches and risks you might be worrying about. It’s easy enough to sit down and plan out a few possible dates over the next couple of months without telling your girlfriend or wife about it, giving you the chance to surprise her on the day with your apparently spontaneous suggestion. Yes, there’s a bit of subterfuge here – but it’s all for a good cause.

So if you know there’s a restaurant she’s got her eye on, go ahead and make a reservation for a couple of weeks from now. If you’re planning to see a movie together, look up an interesting billiards hall in advance that you can suggest on your way out of the theater, instead of just going straight home or to one of your regular dives. Now the same old post-movie conversation is enlivened with an embarrassing (and endearing) game of 9 Ball.

The same thing applies for anything that she’s desperate to do but you’ve been dragging your feet over. If she’s been wanting to go to the ballet for some time and the idea pains you to even think about it, book some tickets for a Saturday a few weeks down the line. Scheduling it gives you the advance notice to prepare and come to terms with it for your own fortitude and weekend itinerary. When you then suggest it on the day as something you could do together, she’ll be floored.

Few people can really find the time or money to pull off full-on impromptu vacations throughout the year, so it’s these smaller gestures that’ll keep your partner guessing and show them that you’re serious about being spontaneous. Of course, there’s a risk that this can backfire if she says she doesn’t want to go, so save these tactics for dates that you’re confident she’ll love.

Thought Starters for Strategically Spontaneous Activities & Dates

1. Combine these or tack onto already planned outings.

2. Pick a few, add them to your calendar spaced several weeks apart.

3. Profit.

  • wine bar
  • a local play
  • a self-defense class
  • a local food tour
  • room escape adventure
  • pack a lunch and meet her near her work
  • paddleboats or kayaking
  • booze & painting class
  • jazz or blues club
  • flea market adventure where you separate and both have to buy each other something less than $30.
  • art gallery
  • horseback riding
  • drinks and a game at a pool hall
  • helicopter tour of your city
  • a hike to a secluded romantic spot, or to watch the sunset
  • a sushi bar
  • a weekend farmer’s market where you procure items for a homemade breakfast
  • a couple’s massage
  • miniature golf after cocktails
  • cooking class
  • stargazing workshop/tour
  • improv workshop
  • day-of tickets from places like
  • eat at the bar of a local fancy hotel, talk to other couples who are on vacation, and discretely book a room upstairs from your phone

A Weekend Getaway

Once you think you’re ready to try a weekend getaway, nominal forethought is even more helpful. The first thing to think about is destinations: You need to think of a few spots that the two of you would enjoy visiting, that aren’t too far away and that have reasonably cheap travel options. That way, you have a rough idea where you can get to with little lead time that won’t break the bank or just wind up being impractical. If any of these destinations are abroad, you’ll need to think about where the two of you keep your passports so that you can get hold of these easily – a surprise trip straight to the airport is no good if you need her passport and can’t locate it yourself.

Once you’ve got a few places in mind, have a look at upcoming weekends that you both have free. You don’t want to look too far in advance, as that makes it that much more likely you’ll end up invited to something you can’t get out of, ruining your plans. Try and avoid anything too close to the holidays or family birthdays too, just in case. Stick to a weekend within the next month or two that you’re confident will stay free.

You can sometimes get away with leaving travel tickets until the day of, but if you’ve picked a spot you can drive to then you’re in an even better position, as there’s no need to worry about tickets at all. If you’re concerned flight or train tickets might be pricey on the day, you can always book in advance, but make sure you opt for refundable tickets if possible to avoid the risk of that money going to waste should the surprise not work out.

Accommodation is the next big step. What you want to avoid is finding yourself stuck in a city you don’t know, wandering the streets looking for a hotel, which will likely feel a lot less spontaneous and exciting once you’ve been doing it for three hours. This is one thing you do want to book in advance if you can. Knowing you’ve got reservations in a nice hotel or bed and breakfast means you avoid the risk of arriving and finding that everything’s been booked up because there’s a conference in town. However, the best deals are often available the day before or day of due to unfilled inventories in larger cities, so consider searching at the departure gate.

Of course, getting somewhere and finding a hotel is only half of it – you’re going to want to find some stuff to do while you’re there. With a bit of luck, you’ll have picked wherever you end up precisely because you know there’s some specific activities you’d like to try, be it visiting certain tourist spots or museums, trying certain food or giving a particular sport a go. If you’re visiting for a weekend, it’s worth planning ahead and booking for one meal at a great restaurant and one good afternoon activity. Beyond that, it’s best just to have a few options in the back of your mind and leave it to the day – having a tight schedule locked in is an easy way to sap the fun out of what’s meant to be an exciting, spontaneous trip, and leaving some free time gives her the chance to have a say in what you get up to.

The key here is to be open to anything. You’ve already thrown yourself into the deep end by organizing a short notice trip, so now’s not the time to put your foot down and stick to what you know. Impress your partner by being open to things you normally aren’t, especially anything you know they’ve had their eye on. If it turns out that the opera’s in town the night you’re there and neither of you have been before, why not give it a go? Or maybe there’s a one-off music festival, or the weather’s perfect for mountain biking – whatever it is, use the trip as an excuse to try new things together. You’re already out of your comfort zone, so you might as well make the most of it.

Strategically Spontaneous Weekend Getaway Checklist

All that’s required for an amazing impromptu trip.

  • Determine destination
    • Consider monuments, historical sites or historic downtowns within driving distance. It’s not a middle school field trip, it’ll be a good time. Promise.
    • Surprisingly, short jaunts on planes can be cheaper than driving, and allow you to travel farther.
    • Find a musical artist she loves, look at the tour schedule, and get tickets in a city the two of you would like to explore. Save that surprise for the night of the show.
    • If she moved around a good bit growing up, take her to the town that she was born in.
    • Big, typical places like New York City, Chicago, Las Vegas, Hawaii, San Francisco, Seattle, etc. are fun, but a weekend in a beautiful place that rarely makes the top must-see lists for twenty-somethings will be unforgettable and are great weekend trips, depending on where you live. Victoria, Canada; Jackson Hole, Wyoming; Austin, Texas; Nashville, Tennessee; Portland, Oregon; Big Sur, California; Montreal, Canada; St. John, US Virgin Islands; New Orleans, Louisiana, etc. Think small.
  • Find a place to lay your head for at least the first evening. This will make things much easier once you’re in town.
  • Discover at least one activity the two of you can do together.
    • Spa treatment? Local attraction? Walking food tour?
  • Choose a first dinner restaurant. Think nice, local, and classy.
  • Decide when you’ll pop the news of the adventure: At home allows her to quickly pack what she needs. Packing for her in advance is more exciting, but riskier, because you won’t be able to know everything she’ll need, since you know, you’re not her. If this happens, replacing these items while at the destination will be your responsibility.

The remaining freedom in your schedule allows you to stumble on activities, events, and restaurants during your exploring. Because that's really the advantage of being spontaneous, if you create a packed itinerary for any trip you're losing the ability to experience things you come across once you're there. This also gives her some say in the activities of the weekend (read: she's actually doing the planning, but you're still getting the credit for being spontaneous.)

A spontaneous, exciting evening or weekend every once in a while can help break some of those habits and bring some excitement back into your love life. Even if it all goes wrong and you find yourself bored to death by the opera, the simple fact that you were both willing to do something new in the spur of the moment will go a long way to reminding both of you that your relationship isn’t, and shouldn’t be, boring.

So give it a go, and challenge yourself to do something spontaneous with your partner in the next month, whether it be an in-the-moment gig or a weekend away, to remind her just how exciting you can be. It needn’t be scary or risky – a little bit of (secret) planning in advance can help you give the impression that you’re coming up with amazing, exciting ideas on the spot, and might just help save your relationship.

Dominic Preston

A London-dwelling philosophy graduate with a penchant for films, gaming, and technology, with the occasional bit of tennis thrown in there.