How to Wine and Dine a Fine Dime Without Weinsteining

Sexual harassment is real. It’s a looming issue women are forced to deal with on the daily. Regardless of this reality, however, we only decide to talk about it when someone important does something stupid. EYE-ROLL. While these scandals primarily come from situations where what-NOT-to-do should be obvious, what about situations where there is actual ambiguity – like, dating?
I’ve noticed boys seem to struggle when it comes to knowing when or how to appropriately compliment a girl. To clear up the confusion, I’ve created some basic guidelines for cases when it’s appropriate to communicate your physical desires or make sexual comments about a woman’s body.

Let’s Talk About Sex, Baby

So, you’re dating a pretty girl. You’re on your first, second, or third date, and you’re eager to let your lady know you appreciate her appearance. Before you speak, ask yourself, “Is what I’m about to say appropriate?” If you’re the average male, the answer is likely a, “No.” Not to worry! I’ll lay it all out for you.

As a general rule of thumb, do NOT say things like: 

  • You have a nice ass.
  • You’re really fit. Do you work out?
  • That turned me on.
  • I love your legs.
  • You’re so hot!
But what if you really need to make an unnecessary, superficial statement?
Here are some safe alternatives: 

  • You have a nice smile. (Even if you really mean “ass.”)
  • You look like you could kill me with those guns. Do you work out? (Same shit, different phrase. )
  • That made me smile. (Better to get cheesy than to go sleazy.)
  • I love your eyes. (Basic over bigot. Always.)
  • You’re so cute! (This is a prime adjective to keep in your arsenal. “Cute” describes both personality and looks. Such broadness allows room for interpretation.)
If you’re still struggling to grasp the concept of what NOT to do, think about your family and friends. If you wouldn’t say it to your sister, mother, or buddy, don’t say it to your date – that is, until you’ve reached a very specific set of benchmarks.

To make a sexual comment without being a complete creep, you must have unlocked one or more of the following achievements: 

  1. You’ve grabbed ass.
  2. You’ve dry humped.
  3. You’ve reached second base or higher.
  4. You’ve had a particularly steamy make-out session. *In order to qualify as “steamy,” there must be primal pushing, pulling, and heavy petting.
  5. You’ve received an aggressively and undeniably sexual advance from the woman. e.g. She straight up sent you a nude.
DISCLAIMER 1: If you attempted points 1-4 but were repeatedly swatted away or dissuaded, the achievements don’t count. They only count when the woman is consenting and receptive. If you disagree with or are offended by this qualifier, take a deep look into your soul. Reflect on your sexist entitlement. Go on a spirit journey, and stop being rapey.

DISCLAIMER 2: These are guidelines. Despite their inherent genius, life is unpredictable. Nothing outside of a warranty is ever guaranteed.

It’s Not Alien: Don’t Be a Predator

Women don’t like to feel preyed upon. Making a sexual comment before it’s welcome is entirely off-putting and in a lot of instances, threatening. In a recent text conversation, I was telling some dude a completely nonsexual story; he responded with, “I’m not going to lie, that really turned me on.” It was out-of-place and distasteful – a cheap ploy to segue into sex. I’m not a huge proponent of ghosting, but I went Casper on his ass.

Shortly after that incident, two different dates informed me I had a great posterior. With them, it seemed totally appropriate – kinda hot in fact. But why?

Blurred Lines: Hot vs. Creepy

While it’s obvious that level-of-attraction plays a significant part in the subjective experience of a sexual comment,  timing plays an equally important role. Both dates who successfully hollered at my hindquarters were boys I had already unlocked points 1-4 with (I don’t do #5 too often.). We had clearly crossed the boundary of sexual ambiguity and solidified our mutual attraction. The timing made sense.

Take-Home Message

Before you’ve engaged in an activity that strongly indicates sexual receptivity, don’t gamble a sexual statement. If you think you know what you’re doing: How sure are you you’ve never made a woman feel uncomfortable? Just as white people run up in arms when they’re called out for being racist, men are overly offended when called out for being rapey. Stop being offended, and start being conscientious. Yes, it’s complicated. No, that’s not an excuse. Learn how to do it right.

Courtship is a delicate process, and emotional intelligence is key. It takes tact. If you’re too eager and have no self-control, you’re doing it wrong. Socially-aware people understand that vibe and timing are everything. Be aware, and instead of wasting our time, work on your timing.

The socially-advanced get in pants!



9 thoughts on “How to Wine and Dine a Fine Dime Without Weinsteining”

  1. Great tips! I hadn’t thought about it this way before but you’re absolutely right: The achievements must be unlocked before they can make body-specific compliments that don’t offend.

    1. Thank you so much! Yep, one thing that holds us all back is our defensiveness regarding sensitive issues. If we could put aside our denial of our prejudices , we could be more cognizant and able to overcome our inherent biases.

      Please do write your own, and if/when you do, plz tag bbgirl in your post 😀 😀



  2. A good next thing to write is when it’s recommended to do 1-4 without the risk of accidentally sexually assaulting someone. It’s definitely a fear a lot of guys have (but I honestly think it’s mostly an excuse to blame politics for why they suck with girls).

  3. Another brilliant post! About this one: “You’re so cute!” I get that a lot and find it mildly annoying, so it’s not exactly in my box of OK compliments to receive. The way I see it is that I’m a MILF and a Cougar, I’m not a little girl, I’m a WOMAN FFS. Just saying.

    1. Hmm. Interesting point. I guess I like the word “cute,” because as opposed to “pretty” or “beautiful,” it usually has something to do with your personality. Cute is like, “You’re adorable, and I feel warm and fuzzy thinking about you.” Whereas with “pretty” or “beautiful,” it’s almost entirely about looks. I don’t want a guy I have no sexual interest in to comment on my appearance, but if he can give me a dual-purpose, looks-personality praise, then sure, I’ll take it.

      Let’s see . . . What word could be superior to “cute” but not as shallow as “pretty” or “beautiful? The search is ON!

  4. Other than I totally agree,with what you said above,I couldn’t help but to notice your amazing punctuation skills!

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