Ask her out (but not in an elevator)

Part one of our series, The Great Filter: Avoiding the Ick on First Dates

Content warning: Wildly generalizes based on the sluts’ personal preferences and experiences. Gendered and likely problematic. Mostly based in guess culture. Advice may not apply to autistic women. Also, swearing and sex and stuff.

The one true whorelord (blessed be her name) recently wrote about going on dates with men who don’t ask questions. This prompted your helpful sluts to think about first date advice we could offer. We have been somewhat hesitant to write about this, because we rarely go on dates with women. We think dating women is scary and hard! We’ve been on a lot of dates as women, but we weren’t sure our advice would be helpful for non-ladies. Chesed can follow tango, but she can’t teach you to lead. All she can do is look up at you and say, “That felt wrong,” or alternatively smile and tuck her head into your chest (realistically your belly if you’re over 5’8”). That is the lens we’re bringing to this discussion of first dates. We can tell you what feels good and what feels… icky. For any more complex questions, we suggest you find a manslut.

The Way of the Virtuous Manslut

Notes from a Good Male Slut

“But sluts! Why are you giving all these dos and don’ts to men? Women are awful and off-putting on dates all the time! Tell them to behave!”

We don’t doubt that women can give men the ick. We are also aware that people of all genders date people of all genders, but we’re not equipped to write an article about the complexities of masc enby/high femme trans lady dynamics or the dating culture of the Castro. Maybe at some point we’ll write about how women can be more physically and emotionally attractive to men. (Chesed has thoughts on this, as someone who went from a Unitarian 7 to a Unitarian 9 over 10 years. Still a Mormon 2 and maybe a Jewish 6. ) However you, our gentle readers, are mostly men. And we like to satisfy men (please picture Chesed kneeling at your feet and smiling up at you).

Asking women out

Whole books, podcasts, and communities have been created to try to solve the problem of how to get women to go out with you. We don’t have the patience or qualifications to go that in-depth, but we do have a few observations.

Your chances are better in person and through friends than through the apps, even if you live in the Bay Area. Pretty much every app is majority male, and men swipe right and message with very high frequency. Women are much choosier with their likes and messages. On the apps, most women are deluged with messages while most men are sending out messages like sperm. In person, though, women are not asked on dates very frequently. Chesed notes that she has mostly been asked out in public via catcall. For more on this dynamic, check out Man Down Episode 5.

It’s ok to ask women out. Sometimes Discourse makes it seem like it is inherently creepy or morally suspect to ask women out. This is dumb. We understand that you, men, may feel anxious as a result of this discourse. Thus we have provided a checklist for the conscientious man who wants to ask out ladies to ensure she feels free to say either yes or no:

• Is the woman alone with you or in a relatively isolated environment? Unless you are already friends, consider waiting until she is in an obviously safe environment, such as a party, a busy public area, or sitting on her husband’s lap.

• Do you have significantly more power than her? For example, are you her boss or a higher-up at her company, her professor, her mentor, her rabbi, or otherwise in a position where you could have a material impact on her financial, career, educational or spiritual goals? If so, I would strongly recommend not asking her out, or at least discussing the topic with a trusted friend first.

• Is she currently at work? Women at work often have to be nice to you. She may be into you, or she may just be very good at her job. Don’t hit on her in a way that requires her immediate attention. You can safely write your number down on a receipt, leave a business card, or otherwise discretely offer her the opportunity to get in contact with you if she actually is interested.

• Has the lady already said no to dates? If so, the ball is in her court to communicate if she has changed her mind. Do not badger.

Give her an out. You can say something like “I’d like to go out with you sometime if you’re available.” This allows her to say either “Oh I’d like that!” or “I’m sorry, I’m not available,” “I’m busy,” or “I’m polysaturated.”

You don’t need a fancy line. You just need to communicate your interest, confidence, and chillness. The vibe you want to give is that you are a cool person with options. You are attracted to her and want to spend time with her, but you are not going to freak out if she says no. What you say depends on context. Chesed’s husband only asks out women he already knows, and typically says something like “Hey, do you want to have sex sometime?” The key to pulling this off is not his big dick but rather that he is normal and chill if they say no.

If you are asking out a relative stranger, like someone you just met at a party, it may be helpful to give a little detail on why you are asking them out. If a guy asks us out within 2 minutes of meeting us at a party, we can only assume he finds us hot and/or he is playing a numbers game. Neither of those are incredibly compelling reasons for us to go on a date.

You can successfully ask someone out shortly after meeting them if:

1. You are a hot billionaire, or

2. You have incredible charisma and charm, or

3. You provide context (this can be implicit)

For example, one of our friends asked out a lady within a few minutes of meeting her at Lighthaven. This worked because:

• They were both hanging out in a rationalist walled compound, implying shared values/community

• He referenced that they were both going to attend an upcoming themed orgy, drawing attention to similar sexual interests, and

• He was friends with the guy she was already sleeping with, creating a sense of social proof and trust

• He’s actually pretty charming in a feral, might drag you off and fuck you in a closet kind of way

One of Chesed’s boyfriends asked her out via this Twitter DM

Chesed’s other boyfriend asked her out via this text (she had VERY FORWARDLY expressed interest to a mutual friend who facilitated an introduction in which she gave her number). Chesed learned later that this text was workshopped with a Very Seductive Man, who suggested removing words, removing detail, and removing punctuation.

Wes and Jacob have been debating whether women should ask out men more frequently. We’ll let the men discuss that one. We do not recommend waiting for women to ask you out as a dating strategy. Sorry.

Setting up the date

We suggest taking the lead in proposing the activity and figuring out logistics. This isn’t a hard rule at all - if she responds to your invitation to a date with her own idea, there’s no need to shut it down to show that you’re Masculine.

Here are a few principles to keep in mind:

• Start in a public place: Unless you are already friends, she will likely feel more comfortable beginning the date in public.

• Don’t do something you hate: A date should be fun. Ideally, it should be fun even if it doesn’t lead to sex, a romantic relationship, or whatever your definition of success is.

• Allow the possibility of a very short date: Imagine the date is going quite poorly. How early can you (or she) semi-gracefully cut it off? Cocktails or coffee are great for this. Getting a drink can turn into two followed by dinner if you get along well, or you can down your cocktail in 15 minutes and announce you have to run. Avoid activities that lock you in for an hour or more on a first date (e.g., dinner, hikes, movies). A longer first date is more appropriate if you have already met in person. If you’re meeting off the apps/Twitter, one or both of you may realize you are not attracted to the other (or otherwise don’t vibe) in 30 seconds to 5 minutes.

• Consider convenience: Is your location close to transit? A quick Uber from her neighborhood? How’s the parking? It’s a classic choice to pick a bar close to your own place in case things go extremely well.

A few specific first date ideas, in order of Chesed’s preference:

• Alcohol (Cocktail bar > wine bar > beer). Choose a vibey spot with comfy seating which allows you to sit next to each other.

• Ice cream, boba, mochi donuts, or any other treat. Consider something Insta-famous if you want to get to know each other in a very long line.

• Coffee/tea + walk. The walk is optional, only if you enjoy the first part of the date.

• Park picnic. At a minimum, we suggest supplying berries or other romantic fruit, chocolate, and a nice beverage (wine or something else that feels fancy if you don’t drink). Bonus points for a more elaborate spread or particularly nice presentation.

• A walk. A walk to a viewpoint is great, especially at sunset. The walk should be popular or close to an urban area, not isolated, to avoid making her feel like she’s on her favorite true crime podcast.

Getting ready

Mindset

The most important preparation to do is mental. Fairly or unfairly, women can smell subtle desperation and we hate it. We suggest cultivating a mindset of abundance. This can of course be quite difficult to do, especially if you live in a small town in Wyoming and you’ve managed to get the only available woman between the ages of 19 and 59 in 100 miles to go out with you. If you’re not in that situation, congratulations!

A few prompts for cultivating a good date mindset:

• Your goal is to enjoy yourself and hopefully help facilitate fun for someone else too.

• You are about to go do an activity you like with a beautiful woman. Regardless of the outcome, this is a win.

• Relax your asshole? (Look, I don’t know. Nick is very, very attractive to women but he’s also objectively hot, which is cheating. But it seems worth a try.)

Appearance

Basic grooming can significantly increase men’s attractiveness.

Grooming checklist:

• When was your last haircut? Consider refreshing it before the date.

• Does your facial hair (or lack) look like a deliberate choice, or like you haven’t thought about it in a week? If you aren’t sure whether you should shave or trim, ask a lady friend you trust.

• What is the state of your pubic hair? If you want someone to lick your balls, consider trimming.

• Consider trimming your nails (ideally the day before the date).

• Shower and apply deodorant before the date.

Clothing

If you are actually the menswear guy (or otherwise have a defined personal style) you can skip this section. Your clothing should be appropriate to the setting for the date. We don’t recommend going on very fancy first dates, so you should be able to wear casual clothing. With that said, you can significantly increase your attractiveness by wearing slightly better clothing than the average San Francisco software engineer.

Chesed’s recipe for dressing better than average:

• Pants that fit you. Jeans are fine. If you are uncertain whether they fit you, ask a trusted lady friend. If you have no trusted lady friends, you may DM Chesed. (No naked pictures! Keep the balls inside of the jeans!)

• A Henley (muscle defining!) or button-down (can be a casual fabric like linen, doesn’t have to be a dress shirt)

• A sweater. Not a sweatshirt! Not a hoodie! Something like this or this (ok we are aware that the second link calls the sweater a sweatshirt but it is made out of sweater fabric and it looks good. Go find menswear guy if you want a fashion expert, we are just sluts).

• If you live in the Bay Area or it is a colder season, bring one additional layer. You can carry it if you don’t want to wear it. This is because your date may have tried to dress cute, meaning not enough clothing, and we want you to have the opportunity to be her hero and provide warmth.

Environment

Is your date going to come home with you? Probably not on the first date, unless it’s Chesed. But if she does, please treat her to a nice environment. If you wouldn’t feel comfortable bringing a girl home to your place after a date, you are cockblocking yourself.

How to make your room less repellent to women

Closing thoughts

We hope this was helpful, but we think this is a topic where your questions and perspective (especially from men who date women) is crucial.

What is your ideal first date? How do you ask people out? Share your thoughts in the comments below or become a paid subscriber to join the conversation on our discord.

Our next post in the The Great Filter: Avoiding the Ick on First Dates series will be all about the first date itself, including asking questions, escalating physical contact, paying for dates, going home, and follow-up.