(light music)
- What's going on?
My name is Desjoire.
This time, the tables have turned
and I get to go ahead and pick a beautiful young woman
based off of her outfit.
What am I looking for in a woman?
That's a great question.
I think somebody that's able to make me laugh,
somebody that's excited to go and travel, try new things.
And sometimes in between, just kicking it on the couch,
laying back and just having great conversations.
So for me, fashion is a way to kind of show
how intentional you are.
How they like to present themselves
and how they like to go about showing off their brand.
I'm definitely excited
to just pick up pieces of somebody's personality,
and maybe potentially find somebody that I think is cool
and fits into some of those components
I spoke about earlier.
Ay, let's go check out these outfits,
see what these lovely ladies got going on.
I'm excited, let's do it.
- Hello, my name is Cheyenne Washington
and I'm from New Britain, Connecticut.
I'm a very outgoing, fun person.
I love adventure,
and I think that if we were to go on a date together,
we would have a lot of fun.
I think my outfit says about me that I'm outgoing,
but also put together.
As you can see, the pattern is a little wild
but it is a matching set because I do have it together.
I'm very confident.
As confident as this blue eyeshadow looks.
- My name is Brooke Pierson and I am from Atlanta, Georgia.
I think my outfit says, number one, that I'm extremely fly,
I'm extremely icy and I'm just very fashionable.
I think the main bachelor should pick me
because I have a really great personality.
I'm gonna win today, just because I look the best,
I put it on the best, but the other girls are great.
I just, I'm just the most fly.
- My name is Jazzy Harvey
and I'm from Los Angeles, California.
My outfit says personality.
This is not fast fashion.
This is not Fashion Nova.
These are all vintage finds that I went and found myself
from different parts of the world.
So I can hold a conversation, I like talking about things,
and yeah, I'm single and don't play games, so I'm a catch.
I'm pretty confident.
I don't really think about losing.
I wasn't raised that way.
- With great power comes great responsibility.
Let's check out outfit number one, see what we got going on.
- All right, this is my outfit.
I'm super excited and I hope he likes it.
- Right off the bat, I'm digging these shoes.
These shoes are pretty fire.
- Feel me.
- I like things that have a little bit of pop to them.
I'm gonna notice those shoes and just think, "Okay".
- Period.
- There's something going on with her personality
where she sees that this is a bold statement,
and I'm assuming that there's something bold about her, so.
- He's spot on, I'm very bold.
- And this right here is just,
it's got a lot of flair to it.
Typically you would just see this top piece,
but you also have the little bit,
I don't even know what to call this.
- Embellishment, embellishment.
- I was gonna say tentacle but that's not right.
But this is just very cool.
I like how this all comes together.
This lady's very bold.
She really has a great handle on her accessories,
and she understands that those accessories
can really take the outfit that extra mile.
- Okay.
I like that he noticed that, 'cause that's definitely true.
Accessories are so important.
- Loving these earrings, loving the necklace,
loving the shoes.
Loving quite a bit.
Lot of great stuff going on so far.
I think this is, almost like a snake type pattern.
I'm just, I think I'm really starting
to see it all together with this, bottoms.
I'm very curious to kinda see the cut of the bottoms.
I wanna know if they're maybe a flair.
- It's wide leg, it's wide leg.
- I don't see a weakness in this outfit.
I'd love to have a conversation with her,
love to get a feel for her personality, so we'll see.
We'll see if that happens.
- Aww, he's so super sweet.
I love that.
- Outfit number one in the books.
Let's go on to outfit number two, see what we got going on.
- This is outfit number two.
Super excited to see what he thinks.
- I don't think this young lady
is doing any commercials for PETA.
(women laugh)
But what I will say is this,
she'll be warm and she'll be toasty.
- Exactly.
- How toasty does she need to be if we are in Los Angeles?
- Well, I wanna know how tight your pants need to be,
since we're in Los Angeles.
- No shade, it's a beautiful coat.
It's absolutely wonderful.
I have no words.
- I have no words for your ankles.
- I will say, it's a bold statement.
I wouldn't say it's necessarily my style.
- Also, I wouldn't say that your style is mine either.
- Now this is a little bit more my style.
I like things that are a little bit more straightforward.
- Yeah, we could probably share clothes.
- I love black.
Black is one of my favorite colors,
even though I'm wearing green and gray.
- So boring.
Snooze fest.
Good night.
- I almost kinda would love this maybe without the coat.
- And I would love if your pants
were just a tad bit more loose.
- I love these boots.
- I know you love those boots, don't you, girl?
(cat meows)
- These boots, A1, A+, high marks.
- Put them on, put them on.
Work it!
- I just like the leather.
If I saw you walking down the way with these boots on,
I would definitely turn my head and be like,
"Okay, she's got something going on."
I love a pair of black leather boots.
And then the shades.
It's, oh, Gucci.
Let me find out something.
She got Gucci, all right.
I almost wanna put them on.
I am gonna put them on.
Yeah, these are hot.
I ain't stealing your pants, I ain't stealing your tops,
but I will steal your glasses.
I will steal those.
- We know.
- Two outfits down.
That was the second one.
About to go check out the third outfit right now.
Let's see what we got.
- All right, time for outfit number three.
I did forget my shoes, so hopefully he doesn't notice them.
I have cute slides.
We'll see what that does.
They saved the best for last.
- So right off the bat, I have to show you love.
I have this same exact shirt.
- Okay, okay.
- This also was my iPhone background.
I went to an HBCU, so I was a little militarized.
Still am a little bit.
Nah, not really.
- Cute and educated, we like that.
- I read the autobiography of Malcolm X.
Big into black empowerment.
Yeah, I would love to have a conversation with you.
- Yes sir, we can talk about that all day.
- Also, too, the leather.
I can just see you being in the 60s, Black Panther,
out here just helping the people progress
and just fighting for the movement.
- I be doing that and it's 2021.
- It also shows that I think
that we can have a very intellectual discussion.
Again, if you see this missing,
it's probably because I'm rocking it.
- God, all the guys I date love my closet.
It's the worst thing ever.
- I'm feeling this.
Leather jacket is fresh.
Whoa, these socks are high.
- Yeah, I'm tall.
- I'm thinking you might have very long legs.
- Yes, yes.
- Taller than you.
- Skirt's cool.
- What's wrong with the skirt?
- I'm just so fixated on the other two pieces
that I didn't even, the skirt could've been whatever.
Everything else is dope, very fire.
- I'm glad we're on the same page here.
- The slides.
I would say, it'll be hard
to march on Washington with these,
but I definitely see you being cozy, which is cool.
You know how to kick it.
- Cozy girl.
- It's something where I definitely see
how you're also into comfort over high heels
and something that's uncomfortable, which I support.
Also, with the socks, you'd be very cozy, so I'm into it.
This bag is tough.
- Yes, Brandon Blackwood.
- This, I almost think I know the guy that made this.
Maybe I do, maybe I don't.
I might be talking out of my ass.
- You are.
- Yeah.
- But it's still tough.
I'm loving the message.
"End Systemic Racism", we need more of that.
- Say it again.
- This choker right here.
This right here is definitely interesting.
Interesting is what leads to a fruitful
and healthy relationship.
- I'm an Aquarian, so you're gonna get a lot of different.
- This is also interesting.
I'm getting crystal vibes.
Black Panther by day, psychic by night.
- It's like he knows me already, this is crazy.
- Got a lot to unpack with you.
- Let's talk black excellence over some good food.
- Time to hand out some grades.
Not really a fan of grading things,
but we gotta do what we gotta do.
Outfit number one.
I love how it's, to me, I think out of the three outfits,
the most succinct in the sense that it just is very clean.
- I'm glad you could see the whole picture, I really am.
- With that being said, I think I have to go ahead
and give that outfit an eight.
I think it's something where it's very solid,
very straightforward.
It, to me, is very clean.
And again, I started off with the accessories.
I'm a big fan of bold accessories,
so shout out to you there.
Absolutely love it.
I think that this outfit had a lot of potential.
The leather boots, phenomenal.
Absolutely love them.
If I saw you walking down the street,
they would catch my eye absolutely immediately,
along with the glasses too.
I'm a big fan of shades.
Where you lose me is the mink.
- Where you lose me is the pant.
- It's, we're in LA.
- Where you lose me is the shirt.
- It's a little hot for that, you know?
I'm hot and I'm in a cardigan,
so it's something where I just, I gotta just kinda question,
are you wearing it because it's needed,
or are you just trying to stunt?
And I don't mind a stunt,
but stunt appropriately is kinda my mindset.
- No, what it is is that you aren't doing enough.
That's why you feel like it's stunting.
- I'm gonna have to give it around a six.
If I saw you walking down the street with the mink,
I would really just wonder,
"Hey, can we help her out?
"Did she just come off a plane from", my area, East Coast.
But it ain't that cold yet, so even then,
I'd be wondering.
So, have to give it a six.
- And if I saw you walking down the street with that pant,
I would be wondering,
"Is it his girlfriend's or his sister's,
"'cause it's a bit tight!"
- Outfit number three.
You really had me with this shirt.
When I see somebody doing something that I also like,
I kinda become attracted to them a little bit more.
So when I see you rocking this Malcolm X T-shirt,
it kinda made me automatically
wanna get to know you that much more.
- Okay, you talking the talk.
Do you walk the walk?
That's what I need to know.
- The second half,
I'm gonna be a little bit more critical of.
I do like the slides, maybe on another outfit,
but not necessarily with this outfit.
So I think that they're a cool pair of slides,
I just don't know if I personally like how they're together.
- I needed my boots but.
- It was the wrong pair of shoes.
- Yes.
- The bag also gets you a lot of points too.
I have to go with a seven, I have to.
I think when gonna split the difference here,
because I love the message that she's got going on.
You're thoughtful, you're somebody that I would love
to have a conversation with.
Can I, can I change my grade actually?
I have, it's almost a tie.
But it's like, I'd love to kind of get to meet
both of these women, but I know I have to pick one.
Ah man.
- Make a decision.
- Please.
- I'm gonna go with what's in somebody's mind
over what I see.
I'm gonna go with 8.5 here.
That's my final answer,
and it's mainly because I wanna get to know you
based off of what you're about.
End systemic racism, Malcolm X, black empowerment.
To me, that means a lot.
I'm gonna go ahead and say, I wanna get to know you
based off of that alone.
I would date this fit.
- Yeah.
- Period.
- Okay, okay.
- That was a good reason too.
(women talking)
- Wait til he sees how tall you are, girl!
You in for a treat, baby.
- He gonna be like, "She a stallion, she a stallion."
- It's a stallion.
- I'm a little disappointed
because I did think that I was gonna win at one point,
but it's okay.
I did feel like the reasons that he picked the other outfit
were really good, so I respect it.
- I feel several ways.
I'm not even trying to be mean,
so please receive this in the proper spirit.
I personally feel like you came in
and gave the girls nothing.
First of all, your pants are so tight.
You are cute in the face area.
We were all interested to see how tall you are,
'cause it's giving 5'1.
And I know you feel like the mink was too much,
but I feel like your outfit was corporate.
It was like, "I work at Google.
"I wake up at 6 AM every single day
"and have my oatmeal and put fruit in it."
If I would see me walking down the street,
I would say, "Who is she?
"I need to know her."
And if I would see you, I would say,
"Hmm, Brad, Brad."
You gave very much Brad.
- I mean, it feels great.
You guys asked me if I thought about losing,
I said I don't think about losing, and look what happened.
I won.
That's called the power of positive thinking, people.
And I'm excited to hear his opinions
and if he walks the walk that he was talking.
We already got a group chat, so I'll hit you girls latter
and let you guys know how it goes.
- All right, we did the arduous task of rating the outfits.
Now it's time to meet contestant number one,
lady number one.
Let's see what's going on.
So you doing all right?
- I'm doing well, and yourself?
- I'm well.
Are you cold?
You look like you might be a little chilly.
- I'm not.
It's cold outside, but it's not cold in here.
- It sounds like you're more than comfortable,
so shout out to you.
You can make that work.
I'll tell you straight up, I could not wear a mink coat.
- I know.
I can tell.
- Okay, well, excellent.
All right, personality of girl number one was a little cold.
Guess that's why she was rocking that mink.
So onto number two, see if something's a little warmer.
Let's see.
So I have to say,
I absolutely loved everything about your fit.
- Thank you.
- And then seeing it on you too.
I love what you have going on with, I think, eyeshadow.
- Yeah, it's the, I wish you coulda saw this, but it's okay.
- I mean, I'll be honest with you,
it really came down to just kinda,
at the end of the day, intentions.
And again, I think your intentions are A1.
It's obvious that you put a lot of care
and thought into your outfit.
- Thank you.
- It was just something where, yeah, it was down to .5.
- Nah, I know, yeah.
I was so mad when you said 8.5.
I was like.
- I know, I'm sorry.
And I switched it up too.
Hopefully I'll get a chance to see you around somewhere.
- Yeah for sure.
- [Drew] Well, if you wanted to, you would've picked her.
- I didn't pick her.
- Yeah, for real.
- That's my fault, that's my fault.
That's my loss.
Now it's time to meet the woman of my dreams,
the woman who I picked.
Excited to meet her, get to know her,
and see what's going on.
Let's see what happens.
- Nice to meet you.
- So tell me about your fit, the inspiration,
I love it.
- I was just like,
"Let me dress myself like how I would
"if you caught me on the street."
This is what I would be wearing.
- For me, it was something that, yeah,
it attracted me to you right away.
I'm like, I'm stuttering over here, I'm into it so much.
But yeah, I like it.
I like it a lot.
Are you ready to go on this date?
- Yeah, let's go.
- Grab something to eat?
- Yeah, let's do this.
- Let's do it, yeah, perfect.
- Hey, Jazzy here.
The date with Desjoire was great.
I really enjoyed our conversation about our upbringing.
They were really different.
- She's an awesome individual, such a fascinating person.
From her catering business
to her passion for modeling and acting,
she has so much going on and I'm a huge fan.
- But we had a lot in common, and with that said,
I think I would definitely take a second date.
- Looking forward to potentially going on a second date,
something that we're setting up right now,
so keep you updated for sure.
But until then, peace.
(light music)