All Episodes

February 16, 2025 14 mins
Original Air Date: February 16, 2025

Just in time for Valentines Weekend, Dating coach for men expert Connell Barrett has do’s and don’ts for how to break the ice and how he can be your wingman right on-site!
Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Welcome to Sunstein Sessions on iHeartRadio, conversations about issues that matter.
Here's your host, three time Gracie Award winner, Shelley Sunstein.

Speaker 2 (00:10):
It is Valentine's weekend.

Speaker 3 (00:13):
This is the last day of well, I shouldn't say
it's the last day of Valentine's weekend because tomorrow is
a holiday for a lot of people, including myself, And
so maybe you have a three day weekend. So maybe
you have a four day Valentine's Day weekend because Valentine's Day,

(00:34):
of course, was on Friday. And I want to reintroduce
you to Conall Barrett. He is a dating coach for men,
and so let's start out Connall with the dating challenged guy.

Speaker 2 (00:50):
What do you offer the dating challenged man.

Speaker 4 (00:54):
I help dating challenged men get confidence to know that
it is okay to walk up to a woman and
flirt if you do it with some authenticity and charm.

Speaker 5 (01:06):
And I help the dating challenge guy know what.

Speaker 4 (01:09):
To say and how to have great dates and how
to get matches on the apps and ultimately get a
great relationship.

Speaker 2 (01:16):
Okay, let's start with the breaking the ice. You're in
a social situation.

Speaker 3 (01:22):
And you want to meet this woman or man.

Speaker 2 (01:27):
What are the icebreakers?

Speaker 3 (01:28):
What are the what are the things that he can
say and not be like if get that kind of reaction, like.

Speaker 5 (01:37):
You're right.

Speaker 4 (01:37):
Well, the biggest mistake that other so called experts make
is they say, use some pickup line, use something planned,
use something scripted.

Speaker 5 (01:47):
I don't like to do that.

Speaker 4 (01:48):
I want a man to be really genuine and in
the moment and not plan anything. And instead of planning
what to say, give yourself three options. If you see
a woman you want to talk to, you can either
a give her a specific g rated compliment like hey,
I love your glasses, but that's a really cool tattoo.

Speaker 5 (02:05):
Option b ask her a question that makes sense.

Speaker 4 (02:09):
You're at Starbucks, you might turn to that woman and say,
so iced coffee.

Speaker 5 (02:13):
Or hot coffee for you today? What are you thinking?

Speaker 4 (02:15):
And the third option is make an observation, notice something
that's happening and call it out. You might say, boy, man,
it's really busy today, such a long line of coffee addicts.
Make an observation. This way you can find the right
thing to say in the moment. You don't have to
plan anything. And also you're not even hitting on them,
you're just starting a nice light conversation.

Speaker 2 (02:36):
Where do you take it from there?

Speaker 4 (02:39):
Well, there, you introduce yourself, you chat about the thing
you spoke about, the coffee she's drinking, the tattoo of
hers that you like her cool style. And then after
you chat about that first thing, then you say, oh,
by the way, my name is insert name and you
get her name. And now you've gone from two strangers
who are talking about coffee or talk about the my

(03:01):
tie she just ordered at that bar, and now you
know each other's names and you're beginning to get to
know each other as people. So you're moving toward a
connection and from there you can let just a lot
of organic natural chemistry will create momentum in the conversation
of its own.

Speaker 3 (03:18):
Let's talk about online dating or on app dating.

Speaker 2 (03:25):
What are your tips there, Well, the.

Speaker 4 (03:28):
First thing to remember is that online dating isn't dating
until you meet that person, until you meet that woman
in person or maybe have a phone or video date.

Speaker 5 (03:39):
Until then, it's not dating. It's marketing.

Speaker 4 (03:41):
Your online profile is a piece of marketing, and you
want to create a profile that is a good piece
of digital marketing to get you matches on hinge or
bumble or whatever the.

Speaker 5 (03:52):
Dating app is.

Speaker 4 (03:53):
So the first rule of online dating is don't think
of it as dating. Think of it as a piece
of digital marketing. And the best way to market yourself
online is showing your authentic best self with really good
portraits where.

Speaker 5 (04:06):
You're well dressed. So you want one photo of.

Speaker 4 (04:08):
You dressed the way you dress on a first date,
and you also want to show a photo on your
profile that shows you doing something that you have authentic
passion for. So on my dating profile, my girlfriend Jess
now of three years, she loved that I had a
shot of me playing tennis and doing improv comedy. Those
are my authentic passions. So lean into your authentic self

(04:29):
on your profile and think of it as marketing. Don't
think of it as actual dating until you meet that person.

Speaker 2 (04:36):
Well, what sort of information should you include other than
the picture? What are the things you should be saying?

Speaker 4 (04:43):
Your social Security number, your number, your number of women
you've slept with.

Speaker 5 (04:50):
No, don't do that.

Speaker 4 (04:52):
Actually, it's not so much about information, it's about vibe.
You want a couple basic things. She wants to know
what your job is. You want to have your job clear,
what you do or what area you're in. But it's
not so much about information. It's about stimulation. It's about vibe.
So I don't put on my profile. I play tennis

(05:13):
two days a week. I might put on my profile.
I love tennis. My Roger Fetterer comes out when I'm playing,
when I'm on the court. First date tennis lesson, I might.
I might talk about a possible first date on my profile.
So it's not so much information. It's about how to
talk about your authentic self with some emotional stimulation some

(05:36):
it's basically it's about vibe, not about information. A big
mistake that men make is they treat their profile like
it's their LinkedIn. Don't do that, not LinkedIn. It's it's
about love, it's about connection. It's about good emotion.

Speaker 6 (05:50):
I don't understand that I'm now married, but I did
the online dating thing years ago. I've never understood who
thinks the picture of yourself when you were twenty pounds
lighter and lying about your age.

Speaker 2 (06:09):
I've I could not.

Speaker 3 (06:11):
I don't understand it, and yet this is really really common. Yeah,
why do people do this when clearly the person when
you meet in real life is going to be disappointed
or surprised.

Speaker 5 (06:26):
Yeah, I hate it when people lie about their age.

Speaker 4 (06:29):
As a twenty three year old myself, I think that's
a terrible thing to do.

Speaker 5 (06:33):
I'm twice that anyway. Yeah, don't ever lie.

Speaker 4 (06:37):
In fact, it's tempting to have the photo of you
from ten years ago and thirty pounds ago, but you're
going to get found out, so you may as well
lean into showing the other people on the app your
most latest, best, most presentable version of yourself and know
that she's gonna want to meet that same guy swiped on.

(07:00):
She's going to want to meet that same guy on
the date. Otherwise you're going to waste time and effort
and she will probably have a terrible time on the date.

Speaker 5 (07:08):
She certainly won't want to see you again.

Speaker 4 (07:10):
So first rule of online dating, other than the tips
I mentioned before is do no harm, no lies, tell
the truth. But of course put that best, most attractive
foot forward, because it is marketing. But we want truthful,
honest marketing with integrity, not lies and not exaggerations.

Speaker 2 (07:29):
I'm speaking with Connall Barrett.

Speaker 3 (07:30):
He is a New York City dating coach for men,
and you are a big proponent of sober dating.

Speaker 2 (07:39):
Explain, Yes, I'm a fan.

Speaker 5 (07:41):
Of being sober.

Speaker 4 (07:42):
I'm two years sober and myself so part of this
came from a personal choice that I made to just
get healthier. But regardless of how you feel about drinking
in general, to me, I think sober dating is the
ultimate flex because you it's an incredible boost of self
confidence to be able to flirt and connect and attract
somebody without the crutch of alcohol. To be able to

(08:08):
go on sober dates is powerful because it opens up
a whole.

Speaker 5 (08:11):
Other world of different things you can do for a first.

Speaker 4 (08:13):
Date instead of saying, hey, let's get drinks, which is
very cliche and very common. So many women love it
when the guy says, hey, let's go do an activity.
Let's go play a board game, or let's go to
do trivia night somewhere, but not drink.

Speaker 5 (08:29):
Let's go play a mini golf. And when you decide to.

Speaker 4 (08:33):
Go sober, not only can you start finding confidence from
within you, not from the alcohol, but you can actually
more vulnerably and honestly connect with that other person because
you're not using liquid courage or using help from Johnny Walker.
You're finding that courage, that confidence from inside of you.

(08:54):
And so it's a great way to grow as a person,
as a man or a woman if you're single a woman,
And it's also just a great way to really connect
with somebody.

Speaker 2 (09:02):
What made you decide to go sober?

Speaker 4 (09:06):
Well, when I drank, I felt good, but I didn't
want to feel good.

Speaker 5 (09:13):
I wanted to feel great all the time.

Speaker 4 (09:16):
So I felt good for a while when I drank,
but I realized that I was getting in some bad habits.
I needed alcohol to relax after a long day of work,
or I thought I did, and I just didn't like
the way it felt to feel like I needed booze
to feel better about myself or to feel.

Speaker 5 (09:34):
More in the zone and happier.

Speaker 4 (09:37):
So what I realized is, oh, you know what, I
actually feel better, and I feel better than better. I
feel great when I'm getting a good night of sleep
and when I'm not using alcohols as some sort of
a social crutch. And the thing I helped my guys
with when we go out to do in person coaching,
I do in person coaching in New York.

Speaker 5 (09:54):
I'm literally a.

Speaker 2 (09:55):
Wingman with the guy out on the date.

Speaker 5 (09:59):
Yeah, well not on a date out approaching and socializing.
I'll go out.

Speaker 3 (10:03):
Tell me how this works, Yeah, tell me how it
worked recently. Let's say a recent scenario.

Speaker 4 (10:09):
Absolutely, I just had a great night out a few
weeks ago with my client, Rocky is his nickname, I'll
call him Rocky, And Rocky is a forty ish financial guy,
sweet man, single dad, and just not confident, very shy,
not socially confident. And so we went out for a
weekend and I helped him approach women in social settings

(10:30):
and lounges in bars, and I used the same approaching
techniques that I mentioned earlier. I said, walk up to
a woman and either give her a compliment, ask her
a question, or.

Speaker 5 (10:40):
Make an observation.

Speaker 4 (10:42):
And I helped him walk up to different women, and
he went from feeling really in his head about thinking
he had to say something perfect and say some cool
pickup line.

Speaker 5 (10:51):
You don't.

Speaker 4 (10:51):
You don't need to use pickup lines. You just need
to walk up to somebody, be really vulnerable and genuine.
And his highlight moment from that night was he saw
a really attractive woman who reminded him of one of
his movie crushes, an actress he liked, and he walked
up and he said, Hi, excuse me, I'm actually pretty shy.
I don't usually do this, but you look just like
Xyz actress. She's my crush, and her face lit up.

(11:14):
This woman and all of a sudden, they're having a
drink at the bar. They're basically on what I call
an instant date, and it's amazing to just walk up
to somebody be really real and vulnerable. That's actually the
most powerful way to approach somebody. And my rule for
Rocky was you can't have a drink of alcohol until
you've connected.

Speaker 1 (11:33):
With a woman.

Speaker 4 (11:33):
So he was sober when he did that, but I said,
as soon as a woman likes you, I'll let you
have one drink, So he kept the drinking to just
one once he connected with her. So it's really about
getting buzzed and quote drunk, not on alcohol or pickup lines,
but getting buzzed on your own authentic awesomeness and getting
buzzed on meeting somebody and learning about them and finding

(11:54):
out who they really are.

Speaker 2 (11:57):
So where were you the rest of their date that
it became a date.

Speaker 4 (12:02):
I'm literally standing three feet away in case he needs me.

Speaker 5 (12:08):
So a guy might come over to me and say.

Speaker 2 (12:10):
What if he did need to how would he do that?
How would he excuse himself from her and go to you.
How does that work? Did you have like signals?

Speaker 4 (12:21):
I give a signal to a man when I want
him to approach a woman, I put my I point
my elbow toward her so that I don't I'm not
pointing at people because that would look weird. So I
give him I give him signals on who to go
talk to. But once he's talking to a woman. The
nice thing about connecting with somebody romantically is is once
the two people find that genuine, real chemistry, they're not

(12:44):
going to need a lot of help nature.

Speaker 2 (12:46):
Well, what if he didn't? How does he signal that
he needs you?

Speaker 4 (12:49):
He walks three feet to his right and says, hey, Connall,
how do I get her number?

Speaker 5 (12:54):
What do I say?

Speaker 2 (12:56):
Or Hey Conall, do we excuse himself from her? I
mean this whole thing, just I just I'm curious.

Speaker 4 (13:02):
It's okay. Well, sometimes he'll text me as well. If
he's involved in a one on one deep conversation, then
he might just shoot me a quick text and say, hey,
should I.

Speaker 5 (13:10):
Try to kiss her? Or should I ask her out?
What do I do?

Speaker 4 (13:12):
And that's what I'm there on these programs do I'm
literally giving him like real time feedback and help. There
have been times when I'll walk up to him while
he's talking to a woman and I'll literally stand behind
him and I can talk to a guy in a
way that she can't hear me, but he can because
I've done this a lot. And I'll say, Okay, I
want you to brush the hair out of her eyes

(13:34):
and then tell her that you find her really charming
because X Y Z, And he'll do it, and then
two minutes later they're kissing. So I'll I'll if I
notice something, I'll actually do a preemptive move and I'll
go over and tell him what to do before he
needs me.

Speaker 5 (13:51):
That's what a really good coach does.

Speaker 2 (13:54):
How do people get in touch with you?

Speaker 3 (13:55):
If they want to explore Connell Barrett's day coaching?

Speaker 5 (14:02):
Yeah, well, they could do two things.

Speaker 4 (14:03):
One is simply go to my website, Dating transformation dot com.
You can learn more about me and set up a
free call. I do free consultation calls with anybody who
wants to know.

Speaker 5 (14:13):
Hey, how does coaching work? Well? Do you charge? How
that in person approaching work?

Speaker 4 (14:18):
They can go to dating transformation dot com and if
a guy just wants to get more tips, but isn't
looking for any coaching. He can check out my website
How to Get a Girlfriend Podcast. I do two episodes
a week where I give all my latest greatest advice,
and I'm doing a big Valentine's Day four part series
about meeting women in real life, so they can go
to the How to Get a Girlfriend podcast wherever podcasts

(14:40):
are released and find me there.

Speaker 2 (14:43):
Okay, I thank you so much.

Speaker 1 (14:44):
Connor Barrett, You've been listening to Sunsteine sessions on iHeartRadio,
a production of New York's classic rock Q one O
four point three
Advertise With Us

Popular Podcasts

Bookmarked by Reese's Book Club

Bookmarked by Reese's Book Club

Welcome to Bookmarked by Reese’s Book Club — the podcast where great stories, bold women, and irresistible conversations collide! Hosted by award-winning journalist Danielle Robay, each week new episodes balance thoughtful literary insight with the fervor of buzzy book trends, pop culture and more. Bookmarked brings together celebrities, tastemakers, influencers and authors from Reese's Book Club and beyond to share stories that transcend the page. Pull up a chair. You’re not just listening — you’re part of the conversation.

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.