LoSt's Challenge

[lostnumber]

Well, I'm back. Things sadly did not work out with the former GF and things have officially come to an end right around the 1 year mark. Thursday was one of the most stressful days of my life due to a lot insanity I'm dealing with at work. I'm brand new to a management position and I'm coming in during the middle of a major transition, a huge project, and a lot of staff turnover. On top of that my best friend's mom died last week and I had to take Monday off to attend the funeral, which not only added to my emotional burden but also put me further behind at work.

I was in the office from 8 AM until 7:30 PM on Thursday, and got home just in time for my girlfriend at the time to stop over and tell me she didn't want to see me anymore. Our relationship has been on the rocks for a while now, so it wasn't completely unprecedented, but needless to say it wasn't the timing I would have chosen. I'm not going to lie to you guys, I definitely broke down and had to step into a conference room a few times on Friday, it's been a really rough week for me.

But ultimately I think its going to be for the best. We were limping along and the relationship wasn't headed in the right direction, nor do I think that was realistically going to change. Sometimes its better to rip the bandaid off and be done with it, and I'll give her credit for being the one to do that, even though its put me in a lot of pain right now. I've always found that the best solution for a sudden absence of girls in my life is to go out and find more girls. So even though I'm nowhere near emotionally ready for a relationship I'm gearing up to get back on the saddle and get back into the game.

I think I previously boasted that I could take my Tinder system and have two girls I was seeing on the regular within 2-3 weeks. I'm going to give myself a little bit more wiggle room then that. Tonight is UFC 229 and I'm going to complete my monthly ritual of getting together with a bunch of guys to watch the fights. My goal is that by the time UFC 230 rolls around on November 3rd, I have two girls in my rotation. That gives me just under a month to land two fish that meet my standards and keep them on the hook. I'm not sure if I'll be able to do it or not, but it gives me something to shoot for. Based on past experience I estimate it will take ~6 dates to get to that number, and it might take me 20 girls I end up messaging to get those 6 dates. Those are very rough numbers of course.

The first challenge is going to be getting up the motivation to get started again. I've installed Tinder and started swiping, but I'm not sending any messages yet, which is a necessary first step. The other challenge I'm anticipating is that as my standards have increased it becomes harder and harder to find girls that meet them (and it is of course harder to get dates with those girls as well, due to all of the other men chasing after them). My goal is to post updates of some kind in this thread, although I can't speak to how frequently that will happen.

 

[Regal Tiger]

Hey Lost! Sucks to hear that you're going through a tough time, but glad to have ya back!


What kind of management position are you in? Like, what industry and etc?

 

[lostnumber]

Hey Lost! Sucks to hear that you're going through a tough time, but glad to have ya back!


What kind of management position are you in? Like, what industry and etc?

I manage the operations side of Alternative Investments for a brokerage firm. We essentially facilitate transactions for high net-work clients in hedge funds, private equity, other types of non-registered securities.

 

[Regal Tiger]

I manage the operations side of Alternative Investments for a brokerage firm. We essentially facilitate transactions for high net-work clients in hedge funds, private equity, other types of non-registered securities.

Groovy! That your passion?

 

[lostnumber]

I manage the operations side of Alternative Investments for a brokerage firm. We essentially facilitate transactions for high net-work clients in hedge funds, private equity, other types of non-registered securities.

Groovy! That your passion?

It suits me, for now. There are elements of the entrepreneurial lifestyle I'd love to have, but I find the structure of a big corporation helpful for me to be honest. If I was left to my own devices I'd procrastinate and get a lot less done then when I'm plugged into the big machine. As for the area of content, I like it well enough. I've always been fascinated by the concept of money, and the idea that you can make a lot of it using nothing but other money.

 

[lostnumber]

A few updates:

Went out Saturday for a friends birthday and stood around awkwardly accomplishing nothing. Big time waste of an opportunity since I rarely go out to bars, so I'm kicking myself on that. I just sent my first Tinder message a few minutes ago, I've been procrastinating that as well but finally took the first step at least. Hopefully I can send a few more tonight as well.

The best news is that I've reached out to a former fling and hopefully have something lined up for a few weeks from now

Me: Alex, hey! It's Lost. So, I was randomly reminiscing about all of the cute girls I've date that have also lived in Australia, and, well, I'll be honest; it was a fairly short list. I thought I'd check in with you. How are things? Still living in [location X]?

Her: *Laugh Emoji* you always knew the right things to say lost ha. Pretty good! Still living in [location x] with a couple of friends and liking it a lot. How are you?

Me: I'm good! The new job is running me a bit ragged, but it comes with the territory. I managed to convince them to put me in charge of a department somehow, and it turns out it's a lot of work.

Me: Last time we talked I think we agreed to limit our interactions to coffee during the daylight, but I can't for the life of me remember why on earth that would be the case. Would all the boys chasing after you be jealous if we grabbed a drink sometime? It's been too long since we caught up.

The next day
Her: Sorry I passed out early per usual ha. Yes let's grab drinks and catch up sometime!

Me: Excellent! Blah blah blah logistics
Her: Blah blah blah logistics

 

[Hue]

lost,

Good opener with your old fling. What's your rule of thumb with letting girls text back when, generally, it's their "turn" to invest in that sort of way? I just had a ghost / flake situation where it's definitely the girl's turn to invest, but she's leaving for vacation soon and we haven't fucked in 2 weeks. Add vacation on top of that and it could hit a month since I've entered her, and nobody wants that.


Also, it looks as though you're posting in this similarly to a journal. Perhaps consider making one or asking Franco to move this over to that subsection.


Hue

 

[lostnumber]

lost,

Good opener with your old fling. What's your rule of thumb with letting girls text back when, generally, it's their "turn" to invest in that sort of way? I just had a ghost / flake situation where it's definitely the girl's turn to invest, but she's leaving for vacation soon and we haven't fucked in 2 weeks. Add vacation on top of that and it could hit a month since I've entered her, and nobody wants that.


Also, it looks as though you're posting in this similarly to a journal. Perhaps consider making one or asking Franco to move this over to that subsection.


Hue

When you say it's her turn to invest, is it because you've sent her a logistical text about meeting up and she hasn't responded? If you share the messages I can probably give you more specific advice.

There is a fine line to walk between investing too much and not pursuing enough. All other things being equal I'd rather overinvest slightly in pursuit of what I want then drag things out in hopes of coming off more manly and cool. This might run counter to the advice you'd get from others, but it works for me. You can see a perfect example of that in the text exchange I posted here where I doubled up in messages. In theory I could have texted her about my job in a way that ellicited a response from her and waited for a reply (perhaps by tacking another question for her into the end). Instead I went right into my ask, which is that we meet up.

I haven't talked to this girl in over a year, and now that I'm on the rebound I want to establish it she's willing to hook up and not waste time if she's acquired a bf, etc. You can probably see the line I'm walking between not framing things super sexually like I might with an ongoing lover, but also making it clear that this meeting would be romantic in nature. Lots of subtle decisions that go into these things.

Good point regarding the journal, I might reach out about getting this moved.

 

[Hue]

When you say it's her turn to invest, is it because you've sent her a logistical text about meeting up and she hasn't responded? If you share the messages I can probably give you more specific advice.

So our texting / meet ups have basically been texting a teensy bit early in the week, then text to meet up on the weekend. We've actually met up twice and fucked (and I gave her multiple vaginal orgasms), all in the course of about a month.

Our most recent messages are as follows:

Monday
Me: heyy, how was your weekend?
Her: It was good, I didn't do much lol
Her: How about you?
Me: aww, no yacht parties?
Her: More like pumpkin patch party! Haha
Me: turn up lol
Me: just a tad more innocent than what I had imagined
Me: does that mean someone's about to some carving sessions in? (typo on my part)
Her: I'm extremely innocent
Me: extremely(;
Me: any other acts of decency are you're getting into this week? (again, typo)
Her: This week is crazy busy ending with me jumping out of a plane. And then if I live, I will be celebrating in mexico the following week (I thought she was kidding, but as I find out she wasn't)
Me: parachute or trampoline? I usually prefer a nice cozy ball pit to cushion me (=
Her: Parachute style
Me: okay wuss haha
Me: well if you live grab me a plane ticket

Friday
Me: hey Venice what you up to
Her: Hey.. just left the [sports] game but headed home. I have my little one (she has a kid) tonight but not tomorrow
Me: ayy what was the score?
Her: [score]
Me: dang, we looked pretty decent during [season]
Me: well I have a birthday party to attend tomorrow but I'd love to see you.. when are you free?

Saturday Evening
Me: holaa, what are you doing after [city event]?
Her: Hey you.. I'm not sure yet. I have dinner at 7:30 but then who knows
Me: gotcha.. ya I'm going to [restaurant] around 9
Me: then trying to hang elsewhere before the birthday girl befriends her alcohol a little too much
Her: Haha why? You don't mind when I do it..
Me: haha well you can handle your shit
Me: slightly(;
Her: Sometimes. Lol

Two hours

Me: praise to [restaurant]'s mules
Me: how were your dinner plannys
Her: Plannys.. lol
Her: It was good.. I'm just leaving. We went to [bar] at [hotel tower]
Me: ooo keeping it bougie
Me: we're gonna skip to [bar] then I'm a free man

*I call her to no answer after this*

Sunday Afternoon
Her: Happy Sunday funday! I just jumped out of a fucking airplane!!
Me: haha fuck yea Venice
Me: please tell me you snagged a pic or two
Her: Oh yeah, I paid extra to have someone jump with me just to video haha
Me: I need to see this
Me: you freaking out and screaming mid free fall haha
Her: It should be good! Doing anything tonight?
Me: stopping by [area] in an hour or so, have a friend visiting
Me: care to join me somewhere when I'm finished?
Her: Yep, I"ll be out.. we're at [restaurant] now. I've got a few friends in town too

2 hours

Me: hey I'm about done, where's the wind blown you?
Her: Well, there is an after party at [younger bar].. so I think we're going there for a bit. Against all my strong advisement, they still want to go. (sounds oddly flaky)
Me: ah after party for what?
Her: For the [industry] show.. but I actually had to go home. I got a call that my little babe was sick
Me: hey it's your kid, I get it
Me: I'll reroute elsewhere, we can reschedule another time

So, I feel like if I do anything I'll officially be chasing.. you know?

At the same time I could call her and figure out her logistics for mexico - but even that's no guarantee.

Hard to remain outcome independent with girls you really like.

There is a fine line to walk between investing too much and not pursuing enough. All other things being equal I'd rather overinvest slightly in pursuit of what I want then drag things out in hopes of coming off more manly and cool. This might run counter to the advice you'd get from others, but it works for me. You can see a perfect example of that in the text exchange I posted here where I doubled up in messages. In theory I could have texted her about my job in a way that ellicited a response from her and waited for a reply (perhaps by tacking another question for her into the end). Instead I went right into my ask, which is that we meet up.

Yea and it always depends on where you think you lie attainability-wise with the gal I think. Too low and a slight more in you investing can show her you are actually interested in her and she might return it back. Too high and leaving some space in the conversation lets her invest more into you to level it out.

In my case I think any more effort on my part will almost certainly leave me in that "too high" space.

Thoughts?

 

[lostnumber]

My two cents? You're texting without direction a little too much here and there is room for mechanical improvement. Texting is really a means to an end, which is to meet up with a girl and hook up. Don't lose sight of that in your interactions, and make sure to have a concrete plan or ask in place that is strongly worded and compelling. Also, you need to make it fun! A lot of my text convos aren't on my phone anymore, but here are two random examples I pulled up of how I might text girls I've slept with a few times but am not going steady with:


Example 1 (Leading question into a date):
Me: Kaity, have you watched the most recent episode of GoT yet?
Her: No!!! Don't spoil it- watching it ok
Me: Well, I haven't either because my group canceled last night. So I was thinking... Who do I know that's really cute and would be down for pirating some thrones?
Her: Ohhh pick me, pick me!!!

Example 2 (Banter leading into a date):
Me: Alex, how is the week treating you? Have you stormed into senior managements office and demanded a raise yet?
Her: Hey! It's alright. I've been training most of the week. I haven't stormed in yet, but I'm tempted! Haha howve you been?
Me: I've been studying for the series 7 for most of the week, its a lot of material! Next time I see you I can wow you by explaining the difference between using options as a straddle vs a collar
Her: Ohhh that sounds suuuuperrr fascinating *grimace emoji*
Me: What can I say, I know the way to a ladies heart; complex financial derivatives *laugh emoji*
Her: Yeah I think you've nailed it
Me: Speaking of nailing things...
Her: Bahah as soon as I sent that I knew that would be the direction this would go
Me: I was going to say, we should nail down a time to get together here. Why, what were you thinking of?

I feel like you're trying to do number 2, but you're falling into the same boring texting trap that most guys do. Let me write the above example the way most people text

Me: Hey, how are you?
Her: Doing good, how about you?
Me: Been busy studying for a test
Her: Fun!
Me: Yea. I'll tell you all about it sometime
Her: Blahh
Me: We should hang out sometime. When are you free?

I basically said the same thing in my actual example, but one of them clearly pops off the page and is interesting and engaging and the other is depressingly lame. I'm not saying you are texting quite as bad as my made-up bad texting example here, because you do have some good bits of banter, but I think there is definitely room for improvement mechanically. Beyond the mechanical level (what you write) I would say that strategically your mistake is not having a really compelling ask, and not continuing to follow through on it. You want to somehow frame the two of you getting together in a compelling way that she can't say no to and CONTINUE PURSUING LOGISTICS until it happens. I think your asks were rather mundane "I would love to see you, when are you free?" Find some interesting way to ask that compels a response, and then once she commits to getting together pursue logistics until it happens.

Random example:
"Venice, I was sitting in class and thinking to myself... you know what I could use more of in my life? Quality time with plane-jumping bombshells. Preferably ones with interesting stories about Mexico to share. Know any potential candidates who would be free next week?"

Send something like that and I guarantee that even if she is busy all of next week, you will get a response telling you she is busy. Then from there its just a matter of pursuing logistics and finding a time she is free. I think you handled the last exchange fine, but I agree that you are investing too much and texting her too often. I would give it a few days, or until she is back from Mexico, and open with a compelling one text suggestion that you'd like to get together. None of this "how was your trip" bullshit.

Hope that helps!

 

[Hue]

Lost,

Yo, thank you for the helpful criticisms. You spelled out very well how guys get trapped in such a texting sequence and what ways you can use to make conversation more fun and sexual, without getting too lost in a directionless conversation. Much appreciated.

I used my version of your opening text on my two new favorite partners and got great responses, one even sending me a picture of her to suggest she be the "candidate", which opened up some fun banter. The other I got a good response, but alas she was on vacation. By the time she told me what day she's back (without me asking) I already had scheduled things with the other.

Muchas gracias amigo.


Hue

 

[lostnumber]

Glad I could help