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March 14, 2025 15 mins

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Intro:

In today's episode we're diving into the tricky world of weekend getaways and why they often backfire for men hoping for romance.

Host Robbie Kramer explores why taking a woman on a trip can lead to the friend zone, and what you should do instead to avoid this common pitfall. Robbie shares stories of clients, including Chris, who faced disappointments after flying women in, and offers insights on how to successfully navigate long-distance dating scenarios.

We'll also uncover why matchmaking services might not be the best solution, and the power of building a social circle to enhance your dating life.


Timestamps:

00:00 "Weekend Getaway Romance Missteps"

03:30 New Year's Misadventure in LA

08:19 "Assessing Relationship Readiness"

10:35 "Long-Distance Dating Dilemmas"

14:14 "Build High Status Social Circles"

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Have you ever taken a woman on aweekend getaway in hopes of a
romantic encounter, but somehow ended up in the friend zone?
Maybe it was even her idea, and when things went S, you felt
resentful and like he'd been cheated?
Well, if that's you, you'll wantto tune into this week's
episode, where I breakdown the weird and counterintuitive
reason why these trips backfire more often than not, and what

(00:20):
you should do instead. You're listening to the Inner
Confidence podcast. My name is Robbie Kramer, I've
been a coach since 2007 and I'vehelped countless men rapidly
achieve all of their social and dating goals.
My mission is simple, to help you position yourself to meet
stunning women, make awesome friends in route to becoming the
most confident and attractive version you can possibly be.
I am obsessed with giving you the most leveraged ways possible

(00:44):
to win the game. So stick around, let's go.
If I had a nickel for every timea guy told me a sob story about
how he went on a weekend getawaywith a girl he was really
excited about and didn't get laid, I, a rich man.
OK, maybe I wouldn't be super rich, but at least a few dollars
richer. And that's, that's a lot of
nickels. A couple of nights ago, I spent

(01:04):
two hours on the phone with the distraught client.
Let's call him Chris. His real name is not Chris, but
we'll call him that. And Chris met a really hot
color, a MILF and divorcee, through a matchmaking service.
Spoiler alert, I'm going to tellyou later on the end of the
episode why matchmaking servicesare mostly useless, so stay
tuned for that. And the problem was Chris lives

(01:25):
in California and this woman lives in Miami, and they were
set up through the matchmaker. They had an amazing first date
which involves some making out, and then they saw each other
again the next night, which involved a little bit more
making out. He disregarded my advice, didn't
follow the dating protocol, instead did like these long
fancy restaurants. And this woman is very wealthy

(01:49):
because she was married to a very, very rich man.
And she has, you know, a very high expectation of a lifestyle.
But she was really cool. And he was really, he was really
into her. So he didn't listen to my
judgement. And he invited her on a romantic
weekend getaway to Northern California in wine country.

(02:10):
He was hoping that that would bethe way that they finally sealed
the deal sexually. So she shows up.
He went for the kiss kind of immediately, to which she didn't
reciprocate, you know, kind of gave him the cheek.
And they spent the next two to three, you know, three days, two
nights having lots of getting toknow you conversations, more

(02:32):
expensive dinners and no sex. And as you can imagine, he was
quite distraught about this. And afterwards he he thought,
well, I mean, why, why didn't you want to sleep with me?
Like what was going on? Maybe I it was because I didn't
buy her a first class ticket andI bought her like, you know,
economy plus. And she's used to flying first
class. Like was she trying to just be a

(02:53):
gold digger? Like he was totally befuddled
about why they weren't sexually active.
And it made even worse. He totally caught feelings for
her and spending three days without sex just made him more
frustrated and even more into her.
And you know, this story is not unique.
It's happened to almost every client I've ever worked with
who's over the age of 30 and hasthe resources to fly a girl in.

(03:15):
And it's happened to me a handful of times too, before I
learned the hard lesson. The worst one for me personally
was a girl I met in Paris. We had an amazing night
together. This is back in 2016.
But she wouldn't wouldn't reallylet it go beyond kissing and
cuddling. She spent the night, but no sex
happened. And you know we could.
We stayed in touch for the next few weeks and decided that it
would be fun to have her fly outfor New Year's.

(03:37):
I had some miles to you. So she came out to LA and we
decided to make it 10 days because of course, like, why
would you travel, you know, halfway around the world for
such a short period of time? And I had a trip planned with
some good friends. Some of my cousins were going as
well. And I didn't really consider the
consequences. The day she arrived, she was
standoffish. She wouldn't kiss me.

(03:58):
Then she started talking about how she's not fully separated
from her ex-boyfriend Jacques, which made it even worse because
I had seen the father of the bride.
I had the picture of this Frenchguy who was like totally cock
blocking me in my head the wholetime.
You know, it may be really upsetthat she was like, she flew all
the way over and then she wasn'tinterested.
So I got pissed. I invited another girl to come
over, had sex with her in the other room and hopes to make,

(04:21):
you know, this girl jealous, butshe didn't really seem to give a
shit. And then I had to spend 9 more
agonizing days with her until she flew back home.
No sex, which was frustrating because of course she was really
hot. She didn't really want to kiss,
but she wanted to cuddle every night.
Go figure. And this just like the example
with Chris, This girl was super excited to come out.
It was even her idea to visit inthe 1st place.

(04:42):
So why do these situations so often backfire?
How can these women fly all the way for a visit and suddenly
have this change of heart? Are they just trying to get a
free trip? Is it some sort of weird gold
digging agenda? So let's really dive in and
unpack this so you never have tosuffer this fate, which is
obviously a massive blood of your ego, big expense, and a
waste of your time. So when it comes to seeing a

(05:03):
long distance girl again after apromising first encounter, you
have four options. The first option is to accept an
invitation to stay with her at her place if she invites you.
Option 2 is meet her somewhere for a getaway, Option 3 is fly
her in to stay with you, and option 4 is casually hit her up
when you're back in the city andtry to just schedule another

(05:23):
date. For the the love of God, never
agree to option one. Never.
Which is accept an invitation tostay with her even if you've had
sex a couple times. You know this wouldn't be a big
deal if you had sex many, many times, but anything really less
than like 10 and you're going toend up in a really bad spot with
her likely losing all interest in you.
The reason being is that you force her into the masculine

(05:44):
frame when she is hosting you. She's going to feel obligated to
entertain you, to take care of stuff, to make the decisions on
where to go, what to do, when todo it.
And this is the masculine frame and I've personally lost a
couple girls by making this mistake and I've seen countless
clients and friends suffer the same defeat.
The worst thing I've ever seen was a guy I knew in Israel.

(06:05):
He met this girl on a birthrighttrip that I went on and they
were hooking up the entire trip.Everything was all good.
She invited him to come and staywith her in Chicago.
And after he he left a week later in the group chat, she
started talking about how he sucks in bed and he has a small
Dick and he's such a loser. And she had to show him around

(06:26):
and she like, couldn't wait to get rid of him.
And, you know, obviously the sexwas good in Israel.
They were having sex. No problems with the size of the
penis there. But that's what happens when you
make a woman into, you know, when you put her in that
masculine frame and you make hermake all the decisions, she
loses interest. So let's discuss option 2, which
is meet her somewhere for a getaway.

(06:46):
And this is obviously the thing that happened with Chris.
And if you've already had sex, this this is a decent option.
But if you haven't is really, really dangerous.
The reason why trips fail is dueto the feeling of obligation.
When you're planning the trip, it all seems good and fun,
exciting, but the problem doesn't rear it's ugly head
until it's too late. It happens right when she

(07:06):
arrives and she's overcome with this feeling of obligation and
pressure to be sexual. You know she knows how much
you're investing to make it happen.
Even if it's not expensive, thatdoesn't matter.
It's the time investment that really matters.
And now she's stuck with you forhowever many days.
And if she doesn't put out, she's going to feel like she let
you down and disappointed you. And that's an icky feeling.

(07:27):
In fact, it's so icky that she will lose all desire to be
intimate with you at all. You know, an obligation is the
lethal killer of desire. Let me repeat that.
Obligation is the lethal killer of desire.
When you guys met the first time, there wasn't any pressure,
no obligation, just two people connecting, having fun.
Of course, you want to continue the good times, so you schedule
the trip. But then she shows up, she's

(07:49):
kind of transported to this other headspace and she can't
get out of it. There's basically nothing you
can do at that point. You're both trapped and you have
to serve that time together. Obviously, if you've already
slept together, there's no pressure and these sorts of
trips can be a ton of fun. So if you're dead set on doing
something like this, you can be successful, but you you need to
go way out of your way to minimize any feelings of

(08:10):
obligation. So I would offer to stay in a
separate room. You know, I'll say, hey, you can
take the room. I'm gonna take the couch so she
doesn't feel pressured based on the sleeping arrangements.
And obviously that won't actually matter once you re
establish the physical intimacy,you know, you're making out.
Things are escalating later thatnight when you guys get there.
But most importantly, I would really check to see if she's
qualified enough to, you know, to do in the first place.

(08:33):
If you really believe that you will sleep with her, it's going
to be a self fulfilling prophecy.
But if you don't, that will alsobe self fulfilling.
So ask yourself, how far is she along that attraction ladder?
Is she super flirtatious? Is she kind of using sexual
innuendo over text? You know, if you believe it's
on, you're probably good. But if you're questionable like
Chris was probably 8, and if she's not, then you really, you

(08:56):
know you're running the risk of spending a few days sexless.
And if sex doesn't happen on that trip, you're never going to
see her again. The friends on text always
ensues. Let's discuss option 3 next,
which is flying her to you. This is by far the best option
if someone needs to fly somewhere.
You'll be the host. You'll make all the decisions,
You'll be commanding the correctmasculine frame.
You can offer to have her stay in the guest room and do all the

(09:17):
things to minimize pressure or obligation.
If she's getting the sense or ifyou're getting the son she's
feeling any. This is no different than
homecourt advantage in Major League sports.
The home team has a significant edge over the visiting team.
The last option is to forgo a trip entirely, which is the
safest and best option by far. Remember, the challenge of
dating a remote woman is that itwill require some sort of

(09:39):
travelling to even see each other.
But instead, you can just make up a business reason why you got
to be back in town. You know to see her again, you
should have other prospects lined up in that same town.
You can basically like instead of him going on this trip, could
have just gone back to Miami, you know, even asked the
matchmaker to line up more dates.
And this is going to minimize pressure, going to kill all
expectations. And you can just continue on a

(09:59):
normal dating path. And then once you sleep
together, then you can do the trip.
So if you disregard all of my advice up until now and do the
trip anyway, here are some critical pieces to make sure
that you've implemented. My suggestion is to only agree
to a trip length of two nights, three days, because you run the
risk of overdoing it. Of course she's going to want to

(10:20):
do a longer trip, but that's a booby trap because spending an
entire three days together is really a long time, especially
with someone you barely know. Unfortunately for Chris, the
sort of dating he does leads to a lot of these sorts of trips.
He has three young kids and the Bay Area is a super competitive
market. So he's hired this matchmaker to
get him hot leads in New York, Miami, LA, But he doesn't live
there. So he has to, you know, go on

(10:42):
these dates and he wants to continue and he's too impatient
to go back to their cities and go on more dates.
So he does the flying out thing.And even though this
occasionally works and he does get lucky and the girls hook up,
way more often than not, they don't.
And it's just a total loss. The other problem is he keeps
going for women in their mid to late 30s.
And we make fun of him in the community because he keeps doing

(11:04):
this. And we call it Project Long
Distance Old Jaded Girls. Instead of hunting for these
women via matchmaking services, we tell him he needs to build a
social circle and farm local cool girls that aren't just
immediately trying to, like, have more children.
And they'll lock a guy down. You know, women who are in their
late 30s are usually looking for, you know, a big time

(11:27):
commitment. And he's looking to just kind of
like fly out and and hook up. And yeah, he's looking for that
too, but it's just the, the, thesetup is terrible.
So the other thing is if he wereto find younger women, he's
going to look like a king to them.
His wealth and life experience is actually impressive when
compared to the, you know, younglosers their age that are that
these women are used to dating right in their late 20s, mid

(11:49):
20s. Instead, he's opting for girls
with shit logistics thousands ofmiles away who are comparing him
to like, Jeff Bezos, like dudes.And all of a sudden his offering
is way less impressive. So before we wrap this up, I
told you earlier I would tell you why hiring a matchmaker is a
very challenging and often moneywasting option.
The biggest reason is that high value women understand that only
low value men hire matchmakers. A truly high value man would

(12:13):
have a network of other high value people around him, men and
women, and this network would lead to an abundance of dating
options. So hiring a matchmaker signals
you've got a weak social circle and you're probably not that
cool in the 1st place. Also, you have to consider which
types of women are courted by matchmakers.
The same issues likely arise on their side.
You have women who are super busy, career oriented, they
don't have time to invest in a social circle.

(12:34):
And this is even a way bigger red flag because women are
infinitely more likely to get pulled into a social circle just
because they're beautiful. So odds are she's going to have
some major personality flaws or she'd make a very poor partner
because she's so focused on her career.
And you're going to be the passenger in that relationship
instead of being the captain, she's going to wear the pants.
And that means no sex for you. Matchmakers often rely on like

(12:57):
basic criteria, age, income, location, general interest.
And that really doesn't. It just skims the surface of
attraction. And they usually focus on
external traits. They ignore deeper compatibility
factors like values, life goals,personality quirks.
And most matchmakers get paid per client or per introduction.
Their main goal can be quantity over quality.
So you might go on a bunch of lackluster dates.

(13:18):
And when matchmakers set you up with someone who looks good on
paper, that doesn't mean you're going to connect in person.
You know, real chemistry develops over time through
shared experiences, common mindsets, subtle interactions.
Matchmakers really can't force that spark.
So This is why I always say the ultimate goal to win the dating
game is cultivating a social circle.
Playing the long game with all your leads by befriending as

(13:39):
many beautiful women as possible.
Delay gratification. You're going to win big in the
long run. Worst off, relying on a
matchmaker can lead you to outsource all of your social
skills. And if you don't learn how to
meet and attract women on your own, you'll struggle to even,
you know, do well When a match seems perfect, you'll want to
develop a you know. You need to develop a real sense
of confidence and direction, which comes from experience and

(14:00):
personal growth. So please think twice before
planning a big trip with someoneyou barely know.
Too much pressure kills desire. Let things unfold naturally.
Build true attraction and keep the logistics simple.
Build a social circle. Take a smarter approach to your
love life. Out of all the guys I know, the
only ones who managed to consistently win the game are

(14:20):
those who built and invested in a high status social circle.
You can certainly approach womenand try your luck on the apps if
you're a Chad, but those strategies simply don't work
consistently to attract top tierwomen and awesome friends in
your life. But for most guys, the idea of
building a social circle can feel overwhelming.
So they continue to hunt for women in their usual ways and
end up settling for a girl they were never really that excited

(14:41):
about in the 1st place. To avoid this fate, join our
community and instantly plug into a highly vetted social
circle of cool dudes to network and navigate your journey with.
You already know it's hard to find wing men because the good
ones don't stay in the game verylong.
Many of our members travel together, end up living
together, build amazing circles and even businesses together
both in the West and in many of the best locations around the
globe. With gorgeous women and low cost

(15:02):
of living, I'm extremely carefulwho I let into this community,
but if you feel like you'd make a good fit, you can apply to
join the links in the description.
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