Talking Points for Life

How to ask someone out on a date
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How to ask someone out on a date

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Oct 3, 2022 10:41 PM
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Last updated October 30, 2023
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“Young lovemaking — that gossamer web! Even the points it clings to — the things whence its subtle interlacing are swung — are scarcely perceptible; momentary touches of fingertips, meetings of rays from blue and dark orbs, unfinished phrases, lightest changes of cheek and lip, faintest tremors. The web itself is made of spontaneous beliefs and indefinable joys, yearnings of one life to another, visions of completeness, indefinite trust.”
― George Eliot, Middlemarch

A single friend recently told me that the dating experience for men is like looking for a glass of water in a desert, and the dating experience for women is like looking for a clean glass of water in a swamp. It’s rough out there. This guide gives you confidence in your noble pursuit of love.
Bon chance, lover! <3
What dating is like for men
What dating is like for men
What dating is like for women
What dating is like for women
Author’s Disclosure: This guide is written from the perspective of a woman for men. She welcomes any and all contributions, suggestions, and disputes. Courtship is a cat that can be skinned in more than one way.

Asking a Stranger

Start Here

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With the world being the absurd place it is, there is a thin and blurry line between charming and creepy. And here’s a disagreeable truth: a lot of the times the line is determined by how attractive the other person finds you. It’s hideously unfair, but so few things in life are. However, there are a few things you can do — and definitely not do — to put your best foot forward.
Don’ts for strangers:
  • Approach a woman if there is no one else around (e.g., alone in a parking lot)
  • Approach if she is busy
  • Approach if she is on the phone or has headphones in
  • Look at the floor or worse — her breasts
  • Touch her
  • Linger, stare
  • Expect a positive reply
Do’s for strangers:
  • Have patience. Be there enough for her to notice you safely, without intrusion, or at the very least, with a well-developed one that doesn't assume anything more than you are taking a gamble with your chances every time you try
  • Look into her eyes
  • If you feel anxious, say so. This can take the edge off.
  • Strike up a casual conversation
  • Offer your number instead of asking for hers
  • Specific compliments that don’t focus on appearances are well-received
Empathy moment: “I had this creepy online stalker. He was actually pretty good looking. Didn't make him any less creepy. The issue is whether it's wanted or unwanted. Attractive people are more likely to be wanted, so they don't run into that issue. I didn't want him because I don't want to date anyone I meet on a forum regardless of attractiveness. He didn't respect that, so that made him a creep.”
Empathy moment: “I had this creepy online stalker. He was actually pretty good looking. Didn't make him any less creepy. The issue is whether it's wanted or unwanted. Attractive people are more likely to be wanted, so they don't run into that issue. I didn't want him because I don't want to date anyone I meet on a forum regardless of attractiveness. He didn't respect that, so that made him a creep.”
- RedditDater

Talking Points

Asking a Colleague

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Seriously. Don’t do it.

HR complaints, awkwardness at work, just no, man, no.
There are 7 billion people on this planet. If you can find someone, you can find them outside of work.
 

Asking a Friend

Start Here

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Note: Know that this WILL change the context and dynamic of your friendship. In other words, “there’s no going back, pal!”
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If you’re confessing your love, go here:
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How to confess your love
  • We’ve known each other for a while now, and I’ve always wanted the chance to know you more.

Talking Points

  • Would you be open to having dinner with me this weekend?
  • No matter your answer, I will continue to be your loyal friend.
  • Listen, if we go out and we don’t vibe, no harm is done. Ok? No awkwardness or hurt feelings. We’re friends who can speak candidly about our feelings. I know that the heart wants what the heart wants, and the mind has very little to do with it sometimes. We don’t get to choose who we catch feelings for. That’s life, and I’m confident that we can both be understanding about that.

The best advice I’ve read on this particular issue

In response to the following question, “How can I ask her out in a way that minimizes the risk of making our friendship weird?
 
Contrary to popular belief, you can ask her out and still remain good friends if she rejects you. This is simply due to the fact that what destroys the friendship isn't asking her out, but rather making a fool of yourself when she rejects you. This worst-case scenario would unfold like so:
You wait for too long and catch way too many feelings. When you ask her out, you're totally lovesick. You arrange a beautifully romantic date in a secluded spot, with rose bushes and everything, perhaps you extend a trembling hand and offer a wad of love poems you wrote for her, and then you're overcome by your feelings and you become a bumbling fool, and you move in for the kiss...
In the movies, she kisses you back with violins and everything. In real life, maybe she does if she's interested. However, if she's not interested and "doesn't see you like that" then...
  • The "beautifully romantic date in a secluded spot" is a tricky situation to get out of.
  • Your investment puts high pressure on her. You created a situation where rejection is difficult, awkward and costly for her.
  • If you drove her there, then you will have to endure all the drive back in total awkward mode.
  • If you start crying (because you're too lovesick, remember) and she consoles you, she will consume the entire energy of the friendship in doing so, after which it will no longer exist.
We haven't hit rock bottom yet. This would be when, the next day, you get drunk, and then a wonderful idea hits you: you're going to ask her out again! Maybe it'll work this time. You start with a long apology, then follow her in the street as she walks away, and then you insist, and then... oh yes...
Your excessive feelings increase the likelihood that you will say the Stuff That Should Never Be Said, like "But I was so nice to you!!! Why do you reject me!!!" which is the totally nuclear option. There is so much wrong in this sentence, she will treat you like radioactive waste for the rest of your life.
Then, of course, the following week you learn that she's dating Chad from the football team, and you conclude that Chicks Dig Jerks and that women are evil for not wanting to date you, such a... a... such a NICE GUY! In other words, you cast upon yourself the cringy curse of the Nice Guy. You die alone, bitter, and a virgin, but at least the fedora looks good.
Another option is:
  • Rid yourself of the fear of rejection, as it is what will cause you to create the worst-case scenario above.
  • Do not fear awkwardness.
  • What you will say when you attempt to initiate the relationship (ie, ask her out) does not determine if she is attracted to you. Either she is already attracted to you because of looks, personality, and past behavior, or she is not. Asking her out doesn't need some magic formula or anything. Either there is attraction or there isn't. Asking her out badly can ruin it, but it can't create attraction.
  • Considering your current friendship, pick a low-pressure setting: you're both swiping through your favorite meat market app and showing each other matches and giggling.
  • At the appropriate point, just mention, "hey, why don't we date each other instead of doing this?"
  • She says yes: you score.
  • She stays silent and gives you the googly-eyed stare: wait five seconds and laugh it off. If you're lucky, she was actually interested and now asks you out.
  • She says no: you laugh it off and go back to browsing. No drama. Not fearing rejection means you don't get butthurt or whiny, and you do not exhibit Nice Guy symptoms…
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      Note: Edited for brevity
 

Further Reading

☢️ Pick-up Lines (use at your own risk)