People
Me: 5'10" asian male, early 30s, switching from a finance career to entrepreneurship
Her: 5'8" asian female, late 20s, last year of top law school, interning at top firm, gym rat, very fit
Background
A close friend of mine sent me a random text telling me his friend thought I was cute, and if I wanted to meet her. I asked to see her instagram, it was private, but the profile looked pretty enough. It also said she's at a top law school, and she also has a fitness instagram.
Texting
So I get her number and begin messaging her casually. She's pretty flaky over text, sometimes not responding for 2-4 days. But each time she apologizes with some excuse for why she took so long to respond. A younger me would have gotten frustrated and let that bleed through my texts. But I was completely cool about it, being sure to send text messages that attempt to hook her for further investment while keeping my investment as low as possible. Eventually she agrees to a casual coffee after work. By the time we actually meet, we're sending strings of 3-4 relatively longer messages, and it's clear she's intrigued and wants to talk more in person.
First Date
We meet at a coffee spot, she's dressed kinda informally, but still sharp, and she's wearing nice makeup and did her hair. I actually think she looks better in person than some of her instagram photos, which is a rarity for girls.
Immediately there's a warmth and comfort between us. She smiles widely when she sees me, eyes beaming, and gives me a hug. We go to order coffee, and before we even order, we build some mutual rapport over our specific favorite coffee brews.
I pay for both our drinks, and we sit down, and begin chatting.
The conversation is great. We talk about both our professional backgrounds, upbringings, shared interests, shared sports--we actually have a lot in common. There's never a lull in the conversation, and she gives me her full attention with smiles and solid eye contact throughout. At heights in the conversation I touch her thigh or hand lightly, to build some sexual tension.
She only has 45 minutes before her next meeting, so I walk her a few buildings over back to her office, feeling pretty good about the whole thing. As we're parting, I end with "so, that was a fun chat...". She replies quickly "yeah, fun fun.... see you around!". Then she runs off into her office building.
Aftermath
That was a weird and unexpected set of parting words. Usually a girl says that if she's not interested in seeing a guy anymore. I text her back to confirm, saying something like, had fun chatting--want to meet again sometime? And she replies that she had fun chatting too, but didn't feel any romantic connection.
So, I was kinda bummed out and also surprised. I thought the date was going really well, and didn't feel any signs of disinterest until literally the last moment of the date.
Theories/Lessons Learned
Anyway, though bummed out, there were some important lessons learned.
Me: 5'10" asian male, early 30s, switching from a finance career to entrepreneurship
Her: 5'8" asian female, late 20s, last year of top law school, interning at top firm, gym rat, very fit
Background
A close friend of mine sent me a random text telling me his friend thought I was cute, and if I wanted to meet her. I asked to see her instagram, it was private, but the profile looked pretty enough. It also said she's at a top law school, and she also has a fitness instagram.
Texting
So I get her number and begin messaging her casually. She's pretty flaky over text, sometimes not responding for 2-4 days. But each time she apologizes with some excuse for why she took so long to respond. A younger me would have gotten frustrated and let that bleed through my texts. But I was completely cool about it, being sure to send text messages that attempt to hook her for further investment while keeping my investment as low as possible. Eventually she agrees to a casual coffee after work. By the time we actually meet, we're sending strings of 3-4 relatively longer messages, and it's clear she's intrigued and wants to talk more in person.
First Date
We meet at a coffee spot, she's dressed kinda informally, but still sharp, and she's wearing nice makeup and did her hair. I actually think she looks better in person than some of her instagram photos, which is a rarity for girls.
Immediately there's a warmth and comfort between us. She smiles widely when she sees me, eyes beaming, and gives me a hug. We go to order coffee, and before we even order, we build some mutual rapport over our specific favorite coffee brews.
I pay for both our drinks, and we sit down, and begin chatting.
The conversation is great. We talk about both our professional backgrounds, upbringings, shared interests, shared sports--we actually have a lot in common. There's never a lull in the conversation, and she gives me her full attention with smiles and solid eye contact throughout. At heights in the conversation I touch her thigh or hand lightly, to build some sexual tension.
She only has 45 minutes before her next meeting, so I walk her a few buildings over back to her office, feeling pretty good about the whole thing. As we're parting, I end with "so, that was a fun chat...". She replies quickly "yeah, fun fun.... see you around!". Then she runs off into her office building.
Aftermath
That was a weird and unexpected set of parting words. Usually a girl says that if she's not interested in seeing a guy anymore. I text her back to confirm, saying something like, had fun chatting--want to meet again sometime? And she replies that she had fun chatting too, but didn't feel any romantic connection.
So, I was kinda bummed out and also surprised. I thought the date was going really well, and didn't feel any signs of disinterest until literally the last moment of the date.
Theories/Lessons Learned
- Not Showing Enough Masculinity - This girl, and the feel of our interaction were an almost exact match to another girl I dated a few years ago. Top education, top career, very fit gym rat/lots of sports (high testosterone) very social, very type-A, thinks most men aren't masculine/ambitious enough to match her. My theory is that this girl didn't think I was nearly masculine enough, which is my fault. Our conversation was so natural, and the date was so short, that I didn't have any time to strategize about how I wanted to portray myself. Usually, if there are lulls in the conversation, I'll immediately think about ways to sexualize the conversation, or bring up some other spicy topics. So I realize our conversation was fairly wholesome, about travels, hobbies, career, etc. I don't run into this problem often, because usually the mere fact that I meet a girl from Cold Approach already gives me spades of masculinity and daring that put me above most other men she's ever met in her life. So I need to be more careful next time I meet a girl in a non-cold-approach scenario. I'll need to explicitly "over masculinize", and I can't just rely on my vibe/confidence to portray that--vibe/confidence is enough only if the pretext is set from Cold Approach.
- Don't Be Fooled by Conversationalists - Some girls are just really good at making conversation with anyone. You'll feel like you're connecting deeply with them, and you are, because she genuinely likes to get to know interesting people. But once you surface out of the deep end, you'll realize it was all platonic. I realize in retrospect it was 70% me talking about me, and only 30% her talking about her, because she's great at deep diving people. And because people naturally love talking about themselves, if she invited it, it fooled me into thinking things were all going great. I need to recognize this next time, and be sure to build on sexual/romantic tension.
- Not Tall Enough? - When my friend was talking to her, she said she likes tall men, so he lied that I was 6' when selling me on her. It's possible that we would have had a good connection, but she just had a hard superficial limit on height.
- Text Game is Getting Better - I've noticed recently that my conversion rate of number to date is getting better, which was needed to convert this one. There are so many micro-rules in dos/don'ts for texting, some of which actually contradict with each other, for example: "always ask a girl for her schedule before proposing a time" vs. "girls don't like to make decisions, propose a time so they just need to say yes/no". After doing A LOT of experimentation, I've come to a set of important rules that match my style:
- never text on a Friday/Saturday evening, unless it's ONLY an icebreaker greeting after you got her number.
- When asking for a date, say "let me know your schedule, maybe Thurs/Fri evening?". This is a clever mix of "asking for her schedule" for girls who want to give an ideal time, while also "proposing a time" for girls who are indecisive and just want to say yes/no. It is also pretty short and blends 3 questions into one casually (schedule?, Thursday?, Friday?). You generally want to ask one question max per set of texts.
- When proposing a location for a date, I usually suggest 2-3 spots, one will be a coffee/tea place. Another will be a vibey wine bar. This allows her to choose the formality of the date. Some girls like really casual spots, as they don't want to dress up and do a ton of makeup, and maybe they want an easy/quick out of it's not going well. Others will be offended at the cheapness of coffee/tea, and want somewhere nicer, so will choose the wine bar. I don't ever propose fancier dinner spots anymore. Besides the fact that I'm being cheap, it always sets the wrong simp provider precedent, and usually I never see the girl again after a dinner date. The nice thing about a wine bar is that, even though it might be vibey/fancy, usually you don't order a multi course meal + drinks there. Usually you order a glass of wine each, and some light bites. So it's still a nice date spot where she'll dress up, but it's not that expensive, and I always offer to pay and don't feel bad about it. I think there's actually an important component, where her seeing you pay for an expensive meal for her causes her to think you're more of a simp.
- turn off auto capitalization and auto punctuation. I come off pretty formal and less jokey in general just as a personality type. These features pull me a bit more casual over text, which is what I need.
- aim to reply with about 85% the length of text that she sent you. But it's okay to go up to 110% if you need to answer something she said, and then also ask for a date
- bait investment from her constantly, and limit your own investment as much as possible. An example of this would be:
- she texts you "oh I love skiing, going this winter to Colorado"
- you reply "oh I'm skiing all the time too. Almost died in vancouver last january!" <- it's like impossible for her not to ask you "oh what!! how did you almost die???" At the same time, you yourself sent her a short 10 word text, so you've set a chase frame where it seems like she's chasing for more information about you.
Anyway, though bummed out, there were some important lessons learned.
