Now that I’m a more experienced dater, I’ve noticed one particularly new and pleasing development: I’ve gotten much bolder when it comes to asking people out.
Women especially are not socialized to be brave in this way, and I can tell you from experience that once you stop expecting Prince Charming to come to you, it turns out he (and/or she/them) is just about everywhere, waiting to be swept off their feet.
Life’s too short not to be brave — too short to expect someone else to make the first move based on gender or other social norms. But as a self-described introverted exhibitionist, I find it’s not always easy for me to just walk up to a stranger and do the deed, no matter how much my heart may want to. But I am bold enough to employ the techniques below, some of which are for IRL meet-cutes and others which can be employed on Tinder.
Of course, you might still find some people don’t reciprocate, and above all else, you must respect that immediately. But the momentary discomfort of potential rejection is, to me, worth the trade-off of a life lived without what-ifs.
(P.S., if even one person falls in love or feels even a little more alive as a result of using one of these techniques, I will be extremely, wildly happy and would love to hear your story.)
1. Employ some thoughtful, respectful investigative reporting.
As with all these tips, I’m NOT suggesting you do anything to make someone feel uncomfortable. However, I think there is a way to do some thoughtful and respectful investigative reporting on your crush that might leave them feeling flattered even if they aren’t interested. The distinction is all in your approach and intention — and your immediate willingness to back off if the crush isn’t reciprocated.
Let me give you a recent example from my own life: A few months ago, I saw an incredibly handsome masseur in a waiting room and we had some serious eye contact. I thought he might be attracted, only I didn’t know his name, just where he worked. Weeks later, when I was still thinking about him, I decided to call the front desk of his workplace and describe him — arm tats, handsome, dark hair. I Googled his name, found his website with his photo and phone number, and then employed my next technique. Which was…
2. Consider telling the whole, vulnerable truth.
I then wrote my masseur crush a very sincere and long text message telling the whole truth of the story. I apologized in advance if my message was unwelcome or he wasn’t available. (Including this disclaimer is key — if you’re going to be this bold, reassure the person that there is no harm or offense taken if they aren’t interested, and promise you’ll immediately back off.) Sure, I felt slightly creepy, but his phone number was on his website, and we had definitely had serious eye chemistry.
Honestly, he was a hot masseur — I figured this kind of thing probably happened to him all the time. As it turned out, according to his message back, it never had, and he was so flattered! We texted back and forth, I sent him a few photos/my website so things were more even and he had the security of my full name too, and we made a date to go for a walk in the park.
Fast forward a few months, and let’s just say my muscles have never been more relaxed. Considerate bravery FTW, every time.
3. Suggest a skills trade.
Let’s say you have a minimal rapport with someone and don’t want to risk a full ask-out yet because you’re worried it might result in future awkwardness. A good way to feel out if there’s more of a connection there is to suggest a skills trade.
So, for example, if you have a crush on your bartender who you know is trying to launch a side business, suggest they slip you free drinks in exchange for your helping them write copy for or coding their website. You’ll be in contact as a result, and if things are meant to develop from there, they will.
4. Write them a thoughtful letter…
You can also be a little more upfront, which these days, is actually creative. Think, “Do you like me? Circle, Y/N,” only AP level.
For example, I asked out a long-term friend/crush with a kind, handwritten note telling him exactly why I think he’s such an exceptional person and asking whether he might want to go out sometime. Nothing particularly complicated about that, but unusually sincere for this era. Not only was he totally flattered and impressed by my honesty, but it turned out he wanted to go out with me, too.
Even if they’re not interested, a thoughtful, undemanding note is so sweet that it’s doubtful to ruin any platonic friendship worth having. If you admit your feelings — and state clearly that if they don’t feel the same way you’d be totally fine resuming as normal (if that’s true) — you have nothing to fear but fear itself.
5. …or provide multiple-choice options.
Another fun variation on the old-school note is to send a message with three to five multiple choice options for a date. This works well for online messaging, too.
Have them vary in degrees of intimacy, interests, and levels of extroversion, and leave it in their court to pick. Make it clear the date is on you (I’m of the mind that whoever asks the other person out should be the one to offer to pay, gender is irrelevant).
So, for example, it could be:
- A new cool show/museum/cultural event you think they’ll like based on your exchanges
- A meditation circle/workshop/other intimate but substance-free personal growth activity
- A home-cooked dinner at your place, making clear you have no expectations of even a kiss (if this is someone you already know and trust IRL)
- Dinner at a restaurant you researched especially to their tastes
- Dealer’s choice or a dare (they get to suggest a date — or a dare-as-date, like skydiving)
6. Spoil a near-stranger.
One thing that really makes someone stand out to me online is confident, preemptive thoughtfulness and generosity.
I’m proudly vegan on my profile, and I once had a guy I was already interested in offer to take me out to the fanciest vegan restaurant in Oakland. He lived about 45 minutes away and wasn’t vegan, so the fact that he was willing to come to me and had clearly done his research really made him stand out. It’s rare people go for such a nice first date or bold time investment these days. If you want to distinguish yourself, be as generous as feels sincere, whatever that looks like.
7. Suggest a phone date in your bio.
As a rule, I almost always like to have a phone date first. They save time if you don’t have chemistry. This is an excellent first step with a lower barrier to entry than an in-person date. You can even suggest it be capped at 20 minutes if you’re worried about getting stuck.
If you have nothing to talk about, you’ll have avoided spending all that time just to drink and perhaps make decisions that don’t serve you. And if you do hit it off, it will give your budding crush more of a chance to build before the first date. It’s very intimate, in this Love in a Time of Texting Cholera, to talk on the phone. It will make you less inclined to judge the book only by its cover. A win-win!