One of the most popular blog posts I’ve ever written was Nobody Ever Died of Akward–all about getting through the emotional hurdles of risking vulnerability to ask someone out.
Asking people out is simply a willingness to have hard conversations. Now that I’ve had a heck of a lot more hard conversations I know how important developing the skills to have those conversations is to creating a life worth living.
Something that helped me a lot back in my active dating days* was having a script! My Gay BFF used this when he was dating, shared it with me and I LOVE it for two reasons.
One, having a script gives me a framework for vulnerability which is fabulous for a Capricorn. (Or anyone who struggles with facing rejection.)
Two, this script is simultaneously sincere and ridiculous and in a dating relationship I am both of those in equal measure. Might as well weed out the folks who aren’t receptive to that on the front end.
The script is oddly formal. Since I met my BFF in law school** we both communicate in a hilariously formal way and so this script might NOT be for you. I encourage you to play with it and make it your own!
The basic premise is that you’re reaching out to someone to find out the best possible way to ask them out. It’s kind of like asking consent to ask them out while also addressing it sincerely with humor. You’ll propose three options and customize them to your connection with that person.
I tend to default to Option 1: Direct Option 2: Indirect Option 3: Wild card.
Option 3 sometimes is an invitation for them to ask me out if that’s what they prefer. (I tend to be attracted to people with a dominant/big personality and dominance 4 dominance begins with an opening for them to take the lead; even though, by sending this email, I’ve already taken a lead.)
Customizing this is key–use the connection you have already to think through how this person might want to be asked out.
I had 100% success rate using this script; if the success is knowing whether that person wants to go out with me and complimenting them. Everyone who got this script from me was clearly flattered and several times I ended up falling in love or getting laid or a little of both.
One time the response of the person clearly indicated to me they were NOT someone I wanted to date! (It was along the lines of “Because you don’t share an eating disorder with me and you are fat and happy I can’t date you.” That story is for a memoir.)
I wanted to include one of my correspondences as a reference and example. Since my ex-lover Luscious went to be with the Goddess twelve years ago already (!!) I feel I am at liberty to share her words.
Wow, was this relationship worth getting out of my comfort zone and asking her to make out. A little background: we met at a conference we both attended annually and her Facebook relationship status was “in an open relationship.” For the three years I’d known her I thought she was polyamorously coupled.
Dear Luscious:
As you may recall, [my besties] and myself are coming to Toronto for New Year’s Eve. We will arrive late evening December 28 and are planning to leave on Jan 1st. Our exact plans are not yet finalized. So far we know the following:
We are staying with our friend [a mutual she knew].
We’re going to a spa called Body Blitz.
On NYE so far 2 parties have been proposed, including Goodhandy’s.
Everyone we have talked to tells us we should go to your restaurant for brunch [she was a chef]. We want to come for brunch AND dinner.
Luscious, you said yourself that you make the best fried chicken ever, and I’m ready to put that to the test. Would you be so kind as to let me know which dates you are working so that we can plan to be at Disgraceland (love the name so much) when you are cooking so that I can have fried chicken made from your hands?
And also, speaking of your hands, I am trying to figure out the best way to ask you if you would like to make out with me while I’m in Toronto. These things are tricky since people’s open relationships sometimes require pre-negotiation and all of that, so I am trying to think of the best strategy by which you will say “yes, Bevin, I totally want to make out with you” and bounds of your non-monogamy arrangement can be honored and adhered to.
I’ve come up with three possible ways in which I can ask you, and would like for you to let me know which one is going to be the most effective.
A. The direct approach. “Hey, Luscious, are you interested in making out with me while I’m in Toronto? I’ve thought you were totally foxy for literally years and am generally too shy in person to say anything.”
B. The indirect approach. “My bestie just looked up the weather in Toronto for NYE and it looks like it is going to be -14 degrees in real feel temp and I am totally going to be looking for really creative ways of keeping warm. Luscious I have over 20 flavors of lip gloss and am wondering what your favorite flavor is?”
C. The cheesy pick-up line. “Luscious, do your lips live up to your name?”
So think over those and let me know which one will work best.
Also, let me know when you work so we can set up our trip to Disgraceland.
Looking forward to Toronto, despite the crazy ass freezing weather!!
xoxox,
Bevin
The reply, oh the wait for the reply, is the sweet torture of putting something like this out there in writing. It was less than a couple of days but in barely 30 year old Bevin time felt like YEARS.
Dear Bevin;
Thank you for your message. Toronto is looking forward to seeing you, [and your besties].
Tuesday night seems to work best for me. My hands are ready to make you fried chicken and my lips are ready for what ever you like!
See you soon!
Lushy xo.
Success! There’s so much I would revise about how that relationship progressed! Hindsight is 20/20 and I’ve studied so much about communication and relational intelligence. But I’m glad I tried! And I miss her!
She sent me home from our second date with deviled eggs and a copy of her friend’s amazing CD*** that lived in my car until I stopped having a CD player. I’m listening to again right now and continue to enjoy! In my later years I realize now how crucial music has been to my intimacy with people and so grateful for all the intimacy me & Lushy had together.
Okay, you’ve got the script! Now go battle insecurity and ask that person out! Hard conversations are worth it! The time to have them is now! Perhaps after a meal and a night’s sleep.
*I’m not likely to need this script again so I wanted to give it to folks who are more actively dating.
**You know, if six figures of law school debt was worth something enduring it’s this friendship! So grateful for you, BFF! (He asked that I not use his name in this post because he’s now an International Businessperson™.)
***CD stands for compact disc and it used to be how we played music before bluetooth and Spotify. A good CD is “no skips” and “heavy repeat.”
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