The downside risk of making a move on a woman you like but who shows no signs of attraction to you.
In this video coaching newsletter I discuss an email from a 40-year-old viewer who met a woman in his friend group who he got to know and started to like romantically. Even though she invited him to spend time with her on this group trip which turned into what seemed like a dinner date, she showed no signs of attraction. He was focused on his interest while ignoring the fact she showed no signs of interest. He tried to kiss her and it didn’t go well. Then he continued to pursue in hopes she would change her mind. She did not.
It’s a good email to show the consequences of ignoring reality and making women feel uncomfortable in your social circle. My comments are in bold italics like this below in the body of his email.
This guy is 40. He is a single guy living in the Bay area in Big Tech. He met a woman that was like part of his friend group. This is a good email because it shows what happens with the downside. Risk is when you hit on whether it’s a close coworker, which can be very dicey if you work in the corporate world or like in this case, it’s just his peer group, her social circle.
So he was hanging out with this girl. She’s single, newly single, had a bad breakup or whatever. He ends up hanging out with her. She invites him to go to dinner. They go to dinner and he’s thinking, “What was all her idea? It kind of seems like a date.” However, there was absolutely no signs that she was attracted to him. Then they were taking a walk together. A little after that, he goes for the kiss, gets rejected, she kind of gets a little pissed off.
If you ever seen the Dumb and Dumber series where this woman is like, “There’s no way I’ll ever go out with you,” and Jim Carrey’s character says, “So I got a chance.” This guy is kind of funny, but he writes in and details what happens here, it’s just a good email because there’s literally no signs of attraction yet. He’s like, “I think I got a chance.”
I’m a 40-year-old single guy living in Bay Area working in Big Tech. To keep the story short, my social circle after COVID was extremely small and for some reason full of single ladies around my age, but all very platonic and no drama.
That’s always a bonus.
I value this friend group a lot, most my long-time friends live abroad.
In March a new lady joins the group, let’s call her Kitty.
Short for kitty cat.
From the beginning, Kitty announced that she got very hurt in past relationships and is off the market so to say.
“All men, stay away from me. There’s a man embargo in my life. Probably not the kind of thing.”
Remember, you want somebody that’s ready, willing, able and open to dating you, and you want a woman who is easygoing, easy to get along with, not a feisty pain in the ass, grumpy pain in the ass. You want a woman that adds value to your life, not one that’s constantly showing up with a truckload of problems or attitude.
Initially, I didn’t think much of her, however we went on a group trip to a Pacific beach town for 10 days and my affection started growing for her bit by bit. After the trip she invited me hiking one day, which turned into dinner. We had great time together and even though it looked like a date on her terms, there were no signs of attraction coming from her. I made no move at that point.
In following weeks, chemistry started really growing between Kitty and me…
Or at least, that’s what he thought.
…To the point where other girls asked me about it in private. On a weekend group trip Kitty and I flirted a lot, she started openly showing her body off to me, great chemistry. At that point I decided it’s time to make a move, or else I’ll stay in the friend zone forever.
Well, in a situation like this where it’s a peer group and you’re trying to take as little risk as possible, you always got to think, what’s my downside risk if it goes badly, if she doesn’t like me? You can always do the kiss test. Remember, it’s looking into your eyes down at her lips, slowly into her eyes, down on her lips one more time, and then slowly back up into her eyes as you’re talking. If she looks at your lips when you’re doing that, then obviously she’s ready to be kissed and you kiss her.
Especially in a case like this where it’s a close group, he already went on like one date with her. There was zero signs of attraction, but she seems a little flirty and open to it. Again, it’s always best, especially in something like this, to go for the kiss test versus some girl nobody knows. Like, who cares? Because you’ll never see each other again. In this case, your whole group of friends is there and most of them are women.
It’s important, you know, a guy that’s in college and he hooks up with a sorority girl, and instead of keeping it to himself, he goes and brags to his fraternity brothers. They all talk. They share stories. Then it gets back to her that he was talking trash about her. Then she goes and tells her sorority sisters. So now her sorority sisters are turned against this guy. Whereas if he had kept his mouth shut and she’d have thought highly of him, then he probably would have been hooking up with some of the other sorority sisters as well. So it’s important to think about what happens. What’s the downside if it goes bad?
Kitty and I ended up walking on the beach and despite her not indicating she wanted to be touched or kissed, I put my arm around her shoulder and told her I wanted to kiss her badly. She recoiled away from me, told me, “NO!” so I took a step back and didn’t continue pushing. She quickly turned back and we left it at that.
So she wanted to get out, dodge really quickly. So that’s kind of awkward. Now you’ve got to see each other. You’re part of the same friend group. It’s like, that went over like a lead balloon.
Tomorrow, however, I got told by a mutual that Kitty told her about my proposition at the beach and that Kitty is angry…
She’s big mad, apparently.
…That she doesn’t find me attractive physically, hates my politics and opinions, etc. – a complete 180 turn!
Remember, she kind of broadcasts to everybody that she was messed up and is has a mini embargo in her life, so she’s got some issues.
I was also told to stay away and not initiate anything further!
So now she’s like, “I don’t like that guy.” Now the other girl is like, “Oh, he’s a jerk.” If there are other women you were hoping to hook up with potentially in the group, it just doesn’t look good for you, James Bond. Gentlemen, don’t kiss and tell. In this case, he saw there were no signs there, and he knew he probably shouldn’t have done anything, but he did. He got rejected, and it’s not turning out so well.
I was butt-hurt and perturbed, and I didn’t manage to hide it at all – she saw it for sure.
Oof! Just making it worse.
I pulled back hard for some weeks. Then end of summer I go abroad alone, and she starts messaging me directly again!
We practically continued where we left off in terms of chemistry, my feelings for her came back in full swing – I was stupid.
Well, at least you can admit it to yourself.
Once back home, I asked her out on a date for the second time. Kitty again refused, so I decided to cool down and move on. However, she continued teasing me, giving me shit tests, snarky remarks, probing about my past, opinions, etc. I once started chatting this hot girl up, and Kitty came over and warned her about me “being sexist”! Right in front of me!
Oh, clam slammed! Clam slammed by the girl that rejected you. That’s not good. That’s not a nice person. That’s why it can be dicey. He went and rolled the dice. She acts like she’s nice. All is forgiven, “Hey, it’s nice to talk to you again,” and he’s talking to a new girl, and she comes over and drops a grenade right in there. What an ass. Not a nice person.
See? See how this looks? It’s not good. It’s not helping you. This is not projecting the image into your social circle. That is beneficial.
I had enough and decided to have her distance herself from me by asking for a date for the THIRD time. It worked – she made a huge deal out of it, blocked me on the messaging app, insinuated I might start stalking her, the whole nine yards.
She sounds a little fruit loopy. Probably not all mentally there. Remember what she announced in the very beginning? Had a really bad breakup. “All men suck,” basically. I mean, she might as well have said that because if we look how she’s treated this guy, she’s like, “Oh hey,” dangles a carrot a little bit and she’s like, “Oh, you’re a sexist misogynist. Get away from me! Stay away from him, girls. Get him!” It sounds like she’s got she’s got some daddy issues.
I took the block as intended, I’ve been in no contact for two months now, no chatting and zero initiation of anything from my side. I found some new people to hang out with, and am continuing to look for opportunities to date new women. She is still in the friends group though and occasionally we are at same events, although it’s visible from the outside that we are not on good terms.
My question is in case Kitty reaches out, how would you advise me to proceed? Me being friendly to her affects how I stand with that group of ladies, I believe they see my “no contact” as being butt-hurt and weak. Please advise!
Hope you like the story!
Well, she blocked you and you guys don’t seem to get along. The reality is, if one of these other girls comes up and says, “Oh, Kitty said this, Kitty said that,” and you’re like, “Well, here’s your text exchange. Here’s her reaching out to me. Isn’t that odd? So that’s kind of the situation we’re in.”
Let’s say this is highly unlikely it’s going to happen. Let’s just say she reaches out in a few months. She’s like, “Hey, what are you doing?” I would never ask her out, never bring up getting together. Just be nice, polite, maybe send two or three texts back and forth. “Hey, how are you? How have you been?” “Oh, I’ve been great. What’s new?” “Oh, life is great. Good things are good on my end.” “That’s nice.”
Then third or fourth time, she sends a message and you say, “Hey, it was nice hearing from you, but I got to run, talk to you later and just leave the conversation.” You’ll never, ever bring up getting together or going on a date or anything unless she brings it up first. The only date that she’s going to get is a dinner date in the evening at your place to make dinner together. Just like I talk about in 7 Principles To Get An Ex Back, she has to come to your house at least three dates in a row. As long as you hang out, have fun, and hook up on all three dates, then you can meet her out and pick her up, but I would let her do 100% of the pursuing because it’s obvious she will reach out, or she did in the past.
It’s just weird. This is kind of nutty behavior. I wouldn’t get involved with a woman like this, but you asked the question. If you’re crazy enough to get involved with a crazy woman, some guys like that, but I wouldn’t. I wouldn’t recommend it. Like I said, I wouldn’t meet her out, pick her up. I would never mention anything about getting together in any way. If she mentions, “Hey, let’s meet up for lunch,” you’d be like, “Well, I’d be down to do dinner at my place,” and she goes, “Oh, you’re a misogynist. I would never come over for dinner.” “Well, you know what? You need to lose my number and not contact me anymore. Have a nice life.” It’s probably how it should go because shhe sounds like a fruit loop. I wouldn’t mess with girls like this.
I mean, look what she did. She went out of her way to clam slam you and make you look bad to the other girls in the group, and you’re talking to a pretty girl, and she comes over and just dumps a big turd right at your feet. That’s not cool. Probably should limit your contact with that group of ladies. If you do show up, maybe you bring a hot girl with you that you’re already sleeping with because it’s clear this Kitty chick is going to try to cock block you.
I would avoid women like this. Especially when the first time you meet her, she announces that she had really bad relationships. She sworn off all men. All men suck kind of attitude. It’s kind of like a man hating, feminist type of woman. I wouldn’t mess with it.
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