Straight Talk: Hooking Up with a Coworker?

Steve Harvey Official
9 followers
Oct 29, 2026
One of Steve’s viewers has had a thing for his coworker for years and they finally made out - should he pursue a relationship or let it be a one-time thing?
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Video Summary
AI GeneratedA viewer named Will seeks advice on whether to pursue a romantic relationship with a female coworker he has liked for two years, especially after they recently hooked up. A panel of hosts debates the risks and rewards of \"dipping your pen in the company ink,\" weighing professional consequences against the potential for a meaningful relationship.
All right, let's get started, ladies, with our first topic.
It's a question from one of our viewers.
Let's hear his question. We have a tape.
Hi, my name's Will, and I'm from Burbank, California.
And one of the girls that I work with
For a couple years now, who sits on the same desk as me,
I've actually had feelings for
since I started with the company.
I never really thought that she felt the same way about me,
but we were out with a bunch
of coworkers last weekend, and we actually ended up,
you know, hooking up and making
out after that night.
Now I'm starting to think that I might
be able to act a little bit on, you know, how
I've been feeling for the last couple years.
I'm a little nervous because I do work
with her and I see her every single day and we
sit right next to each other.
So I don't know.
Should I go for it?
Okay.
Do it.
Yeah.
What's the saying?
Don't dip your pen in the company ink.
Is that what it is, right?
Look, I know many people who have hooked up at work
and ended up getting married, and they're very happy.
I also know people that hooked up at work,
and then it was super awkward.
So I think you have to have,
you have to know what the consequences are going to be.
I say pass.
I don't know.
I don't know.
I'm waiting.
Mariel, what you think?
I say go for it.
Listen.
The pickings are slim.
The pickings are slim.
Real slim.
You already like this girl.
Right.
Very clearly.
You made the video, so you can't put that genie back in the bottle.
And you could be fired any time for any reason anyway.
Then you don't have a job, and you're still lonely.
Get the girl.
Yeah.
Yeah.
My issue would be
to have a conversation with her
first about... Because my thing is, you work
with the girl and y'all made out last weekend
so you sit next to her every day
and no one tapped the other person
like, hey, so you want to talk about this?
It's already awkward. You know what I mean? It's already awkward.
I would have a conversation with her first
and gauge where she's at with it
before just being like, blatantly
ask her out on a date. I mean, I think, you know,
I agree with both of you guys. I think, you know,
on some level,
YOLO. Like, go for it. You like the girl,
but there's also, there is also the risk of you, you know,
if you decide you want to go there with her and she's,
she turns around and she happens to be crazy, then you, you know.
Okay, now, you got to go for it.
Right.
She could be the one. You've been sitting there
for two years feeling this, girl?
Yes.
Let me, let me explain something to you.
The longer it takes for a guy to get over the fence.
The longer he stays, when he gets there.
But what if she's not feeling it?
What if that was just a drunken night and she wants to forget about it?
But that's why they had to have a conversation.
Well, we need to find out.
Okay, let me ask you ladies something.
Have you ever dated?
Someone you worked with yes, and how did it work out? They know?
No longer work there.
Well, you need a longer couch so I can lay down
Right, I was going to say, it's a much longer day.
Other than water in this cup for that conversation,
it's awkward look the beginning is fun.
You're sneaking around nobody knows
And then it gets dragged out, and then it doesn't work out,
and then you still have to see them every day.
He sits next to this girl five out of seven days a week.
He's with her all the time.
It's really hard when you're in that close proximity
for that amount of time to not...
You know what I mean?
To not get to know a person.
And if you like a person, then that's even, that, you know,
snowballs into you really liking them
because you're with them all the time.
So you develop a rapport and a relationship with them.
So, I mean, it's hard.
But also, if you're in the same industry as that person,
you have more in common with them.
I mean, when I come home and I'm telling my man,
guess what she did at work?
I don't want to start the story over and have to explain who she is.
I need you to already know so we can talk about people together.
You got to go for it.
Y'all tripping.
If you feeling somebody, you should go for it.
That job you got, it's a job.
It ain't a career.
Your job don't pay that much money.
So you're going to miss out on, no, listen to me.
You don't know.
No, really.
It's another, whatever money you making on that job.
He's afraid of the rejection.
That's why I said have a conversation with the girl.
Because if you, you know, if he goes full throttle.
Scared man can't win.
You're right.
You're right.
That's good.
Hey, look, we got to take a break.
We got more straight talk when we come back.
Don't go away, y'all.
Hey you made it to the end of this video.
I got a lot more that you're going to enjoy so just
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