- Hi, my name is Dylan. So you might recognize me from the personality versus appearance video. I guess you guys wanted
me back, so here I am. I'm happy to be here. (upbeat music) - My name is Simone Grossman. I am a professional matchmaker. Three out of my four closest friends are all dating men that
I set them up with. I worked for two different
matchmaking companies. The first client that I ever
met with that I was assigned, actually also got married to her match. And that to me was like, okay, I'm doing the right thing. Like this is something that like, this is the job I'm meant to have. (upbeat music) Hi. Hi Dylan. - Hi Simone. - I would love to hear a little
bit about your background, about your family. - Yes, so I have two sisters,
one older, one younger. - Mm-hmm. - So I am the dreaded middle child but it's not that bad, you know, talking to girls is not as bad as maybe someone
who doesn't have two sisters. Because of that, I have a lot of like
female friends as well. - Are there little like things
that endear you to a person? Like it could be behaviors,
or like a personality trait, like things that you find charming that just draw you to someone? - I feel like it's the
way they carry themselves- - Yeah.
- When they walk into a room. That's the first thing I'm looking for. It's like, oh, do you have a good smile? Do you have a good energy? I'm gonna turn my head and like, okay, who's this person, you know? - Yeah, so we need people who have strong sense of direction. - Yes.
- Outgoing, confident in their own skin. If we were to like distill some
of the most important things that you're looking for in a
partner into like three things, what would those three things be? - Definitely, goal-driven. - Okay. - You have a sense of humor.
- Mm-hmm. - And having that banter
back and forth is, I feel like it's just a need you know, I feel like I just want
to be able to like, say something and then
you say something back and we're just joking around having fun. - Some wit.
- Some wit. - I love it. - There's a certain type of girl I just, do not really vibe with.
- Okay. - More like alternative dressing type of girls.
- Okay. - I can't really put a finger on it. It's just more of a feeling that I have, and it's just like an
energy type of thing. - Totally, yeah.
- I found out through dates, that those are just not my type of girls. But you know, more power to them. And I'm glad that they can
express themselves that way. - And do you see yourself getting married and having a family? Is that important? - Yes, that's something
I'm looking forward to, finding my one true love,
and like having kids, and attending their baseball games, and their soccer games and all that. I want to be a dad. Like I feel like I'd be a great dad. - Awesome, that's really sweet. - I have one question.
- For me? - For you, yeah.
- Okay. - Like, if I'm just vibing with someone who's just completely not
what I told you at all. - Like, how would you approach that? - Nine times outta 10, the person that you end
up with isn't exactly, it doesn't come in the like
shape and box that you thought. So I would really champion that for you. Unless there was something
like a glaring deal breaker. Like if she didn't want kids or something, I'd be like, okay you
might have chemistry, but you're not compatible. But if she's maybe a little alternative, and you actually find that charming, I'd be like that's really cool Dylan, you're like expanding your horizons and learning more about yourself. - Yeah.
- Sweet. [Producer], All right, are you guys ready? - Yes.
- Yes. - Hi. (upbeat music) - Nice to meet you. (upbeat music) - You guys all look so wonderful. - Thank you. I'm Dylan.
- Hi Dylan. - It's so great to meet you guys. It's ready to rumble. So let's do this thing. I do have one question just to
kind of get the ball rolling. If you had to describe your dating life in like a movie title, what would you say? Because I have, I have mine. - Crazy Stupid Love because
love is crazy, and stupid. - What you got? - A Series of Unfortunate
Traumatic Events. (ladies laughing) - Mine is 50 First Dates. Okay, it's. - Oh. - It's been a lot. - My movie title would be Lonely, Oh God, How Long Will This Last? (ladies laughing) - I don't think I've seen that one. - That's a good one. - Okay, I wanna jump in with a question. I'm curious, what is the best like compliment that you've ever received? - That I'm stable. - Okay. (ladies laughing) Well like I got my life together now and like I have a good job. I'm nice and they're like, you're just, you got it, complete. - That's awesome. - I love that. - A couple years ago, one
of my really good friends she told me that like even though I'm not the type
of person who says a lot, I'm like very intentional with my words and she really appreciated that. - That's awesome.
- That's a really good one. - That's a great compliment. - My favorite one recently
has been I love your energy and that says a lot to me 'cause I just wanna have
everyone comfortable in my presence. - I was walking and some guy was like, oh
my god, you're so powerful. And I was like, thanks. - That's awesome. - I think that's special. - What is everyone's deal breakers? - I have a big family. Like I love seeing my
family when I see them. So like it's kind of just
like we're different people if you don't connect with your family. - Your relationship with my little sister. My little sister, she's
like my best friend and I really want the person I'm with to just like be her best friend too. And if you're like not
best friends with her, there's something wrong with you (laughs). - How old's your sister? - She's turning 19. - I have a younger sister who's 19. - Really?
- Yeah, two sisters - Controlling.
- [Dylan] Okay. - So like saying you can't have
friends of the opposite sex, they're like, you can't
go out without him. - Dylan has a lot of
friends that are girls so that's not a red flag, right? - I think that's a green flag. - I think that's a green flag too. - Yeah, it's a green flag, - Openness to change because you know you could
be anywhere on the map but then if you decide
like I am in this place and I wanna be somewhere
else, then you can, you know, pretty much anything
that's negative of you, you can make better. So as long as they have that, I think that it's like all the way up. - I agree with that one heavy because like as just me personally, I feel like I've gone through
a lot of transitionary periods where I've definitely
like changed as a person. So I feel like I would
want the person to be open to you know, growing and like
changing and self-reflecting. So I feel like that's a great one. - And then also, and it's okay if you don't
know 'cause you're young but like do you see
yourself getting married and having a family? Is that something that's
like far off for you or were you born and were like "I always knew I wanted to be a mom." I'm curious, if we wanna go in order. - Yeah, I'm scared of birth. Yeah. (ladies laughing) - Yes.
- Yeah. (murmuring) - I'm not jealous of you guys. (ladies laughing) - Like I love the relationship
that like I have with my mom and I would love to be like the mom that has a relationship with her kids. - Follow up question. Son or daughter, or daughter
or son or like what's the. - Okay, I obviously like love both of them but I've always just wanted to
have like a little baby girl. - Do you see yourself being a girl dad? - Everyone says I'm a girl dad. - Yeah. (murmuring) - I'm like, okay, I can see it. Like, I definitely want a daughter too. I definitely want both. - I didn't have like the
best family like growing up so I definitely wanna
like break that cycle, have my happy little family and I could be the mom that
I always wanted to have and didn't get to have. But I love my grandma. She stepped up, yeah. - Hell yeah. (everyone applauding) - For doing good, grandma. - My dream is to be a mom. I literally work with kids and like, oh my god, I just love kids. I would have like 10 if
I could, but honestly. - That's a lot of kids. - Exactly my point. I really know I'm not gonna do that because I already have like
kids at work so two's enough. - Actually ideally, I
don't think I'd have kids. I want to get married. I've imagined myself being a mom and I think I'd be a good one. I think my only requirement if I have children is at least two just because I would want
my kid to have siblings. - Okay. Is there like a reason why
you're not leaning towards kids ? - You know like shaping somebody seems like a big, really
big responsibility and maybe because I'm
at a point in my life where I'm like that
would be so overwhelming that maybe I can't fathom it.
- Right. - Also global warming. Like climate change is getting bad. - It is. - And I don't want my grandkids. - See what's happening in New York. - Yeah, the flooding, yeah. - Nowadays I'm kind of
just like in this economy, maybe not the best idea but I think eventually down the line, once I'm more financially set, I would wanna have kids. - Yeah, I think it's
definitely very important that you don't bring another
person into this world unless you're ready and capable to. So definitely being financially stable is probably a good idea. - First of all, you guys are
all amazing and so beautiful and I've had so much fun learning about what you're looking for and this is obviously very much based on who I think is compatible
rather than like anything else. So I just wanna make that clear. I'll start with London. I think that you're (laughs) you have a really outgoing
energy, you're very witty. That was something that was
really important to Dylan. You seem super driven and really active so I think there's a lot of
really like great overlap. Melissa, I also felt that like you have just a very like
easygoing like peaceful energy but also like very outgoing and like unselfconscious
which is like really lovely and I loved your answers. So I think that there's
some compatibility there. Cassidy, I felt that you
are like very driven. I was a little unsure about the kids thing because just 'cause that's
like maybe a potential conflict but I also think with like when
it comes to love and dating like not everything is
gonna align perfectly in terms of box checking. Naz, I felt you guys
have medicine in common, which is like really cool. Also, I loved that you
were like very candid about being like discovering like a more boundaried approach to dating and that's something that
Dylan has expressed to me, is like a similar pattern. - One more, okay, okay. - Sorry Jasmine. - You also have like a very
grounded self-confidence and I liked that you were like really open about the things
that you aren't set on yet that you like do everything
a hundred percent. 'cause that also feels
very kind of like congruent with where Dylan is at in his life. So those were the people that I think there's like little
seedlings of compatibility. - I feel like you, you nailed it. (all laughing) Right on the head, she got it. (upbeat music) - Hi.
- Hi. - Hello. - Can I hug people?
- Okay. - Hi.
- Hi. - How are y'all doing?
- Good. - You feel nervous? - A little bit but then I was like you know,
whatever happens, happens. Just have fun. - Is that the type of energy
like you'd be carrying into like a relationship
or like what do you think? - Yeah, I'm very much like allow emotions or feelings kind of flow and go wherever they go. - Mm. - What type of date is your vibe? - For first dates, I think it's good to
have a lot of talking. So I'll do like drinks and dinner. I think that you know,
having a little mimosa or something can kind
of help loosen you up and let the conversation flow. I love doing activities
and like watching movies but I feel like that's best
for like a fourth or fifth date because you wanna spend
like the first couple times really getting to know someone and seeing if you're compatible. - How about you? - First date wise, I'm definitely more of
an activity type guy. - Oh.
- I feel like for me it takes off some of that pressure that you have when you're
first meeting someone. Let's take some of that tension off by diverting our attention to something then we can talk in between and kind of like bounce off each other. What's your ideal second date? - Well I can't sit down face to face. - Okay.
- Yeah, as we're doing that. But I don't like sitting
down and having dinner. I like to like be walking or doing something and being outside. I think the main thing is
just being able to talk. But I would ideally like
second date is like, you know, you get into some of the deeper, not deep, not super deep, but like you get to know each other on more of a deeper level. - All right, I like that, yeah. I feel like we've had the
most similar career plans. So I just wanna ask you like what made you get into
medicine in like nursing? - I've always known I
wanted to help people and I was like yeah I don't
really wanna do med school. I just feel like it's
too long term for me. I wanna kind of get there.
- Right. - So kudos to you for that by the way. - I was struggling. - It's a long journey but it is worth it. I will say that. But when I was in nursing school, I did a pediatric rotation
on an oncology floor and then I fell in love with this like little
two year old that I had and I was like, I kind of love this. Like I love kids so I
was like this is perfect. - I love kids as well. I don't know if that was a parent when I was talking
about them earlier, but- - That's awesome. - I feel like they just
gravitate towards me and we just have, we just run
around, have fun, you know. It's definitely inspiring to see the physician that I work with and how he handles things and it's kind of reinforced my
like wanting to do medicine. So that's, I'm super happy
that I picked the right thing. - Yeah.
- And not the wrong thing. So music. Do you sing? - Yes. - Guitar, piano? - I used to play electric
guitar when I was really little. I had like a black and
white little kitty guitar. - Guitar hero?
- Amazing. - Okay, I've never played that. - No.
- Yeah, I know. Do you have any passions or anything? - I like to cook.
- Me too, I love to cook. - What's your favorite thing to cook? - Oh, I love Japanese sweet potato and with like a really good fish and then some vegetables. - What's your favorite vegetable? There is a wrong answer. - I feel like I'm gonna
give the wrong answer. - As long as you don't say
it, we're fine, we're good. - I would say honestly
maybe like a eggplant. - Eggplant? That's a no, that's fine.
- No. - I thought you were
gonna say like broccoli. - Okay, that's the wrong answer? - That's the wrong answer.
- Interesting. - No, not broccoli. - You said you've been snowboarding for about like four seasons, right? - This is, yeah this will be my fifth. - Okay, cool. Planning any trips soon? - Yeah I normally either go up alone or like I'll meet some- - Solo skier. - Dude, it's fun 'cause you
can be like in your head. - I want to do it so bad-
- You haven't? - But I feel like if I die. - Okay but you're on a
mountain with like people - But what if I'm on like, like a back road or a back country? - But then you can save those
for like the group sessions. - I guess.
- You know? - Are you familiar with love languages? - Familiar? Yeah. - Okay. I'm curious like when
you do really like someone, what are ways that you express affection? - Oh gosh. I do like physical touch
but I'm not a PDA person. Like I like I'll hold your hand
in public but if you're like on me I'm gonna like
please don't touch me. - How do you feel about PDA? - Don't, don't like it. - Cool.
- Yeah, great. - I feel like there's a time and a place and that is neither the
time or the place, okay. - And then I get
uncomfortable even watching it so I'm like why would I wanna
make someone uncomfortable? - Yeah, especially even been
to like Disneyland's just like- - They're like, "Oh baby." - Like, hey relax, this
is a family place, okay? - There's Mickey right
there bro, like chill. - Do you have a type, have you picked up on
like recurring patterns? - I don't. I want their head to be like
physically bigger than mine because no, like- - I don't think I've ever heard that. - I've never heard that. - But if you look at like
couples that look good and it's like oh yeah they work, the guy's head is always
bigger than the girl's because it's weird to like
have like a head like this. - Is my head bigger than hers? - I think it is, I mean. - Yeah, yeah, I think it's bigger. That's awesome. - [Producer] All right guys,
that is unfortunately time. Thank you Cassidy.
- Thank you Cassidy. - So nice guys to meet you.
- Thanks. - I love the big head thing (laughs). - That's so fun. - Thanks Jonathan.
- Thank you. - Nice meet you.
- Nice meeting you. - No, this is gonna be hard. I feel like I've made some
some great connections there. - I think it's between two people for me and I can't tell. I can't tell 'cause
very different energies. - Yes.
- It's between two people, don't you think? - It's between two people?
- Yeah. - How does she know me? (laughs) - [Producer] Do you feel like
you have enough information to make a good decision? - Yeah I think so. It's like a gut feeling as
much as it is like analytical. So there's always room for error, which is the beauty of
matchmaking to begin with when it's a human and not a a dating app. So I'll start with Melissa. I didn't feel that you guys kind of were pulling a similar thread. There wasn't, the conversation didn't
quite become like easeful and I perceive maybe you guys have slightly different senses of humor. You are our first to be set free. - Bye.
(murmuring) - Cassidy, similar thing
about sense of humor and just like banter is that maybe you guys would have a perfectly. I think all of you guys would
have a great first date. It's more I'm vetting in terms
of like avatars in my head of longevity.
- Yeah. - And I didn't quite feel
that energy between you guys. - Okay, watch Suits (laughs). - Next, I would say Naz. You guys have so much in common. I was wondering if there
would be a little bit more like the conversation would take off. I think the kind of like push
pull or like banter thing was maybe not as present as I
felt with other matches, so. - No worries, nice meeting you. - Nice meeting you. - And then down to our final two. (woman laughing) Jasmine, you are just so impressive. You have so much clarity in your life. I think that you guys communicate
maybe in different ways and have slightly different interests. And again, I think just
that like playfulness not to say that you're not both that way but like manifest in
slightly different ways, so. (murmuring) So my final choice is London. - Oh yeah. - I just felt like I barely
had to step in at all through your conversation that there was just like
so much like laughter and like bits. You are slightly different than like what Dylan had told
me as his like tangibles. But like it was like really fun to witness your conversation. Ah, yeah. So that was my final choice for you. - Cool. (people laughing) I agree with everything she said. You know, just think you're
super dope person as well. - Thank you, you as well. - [Producer] So, we have an envelope which Dylan wrote his top pick in. - Drum roll. - Oh my god, I'm shaking. (Dylan laughing) - Why am I laughing? I picked this person because I felt like the conversation
was flowing very well and just long term I feel
like it'd be a good fit. And I also liked the banter as well. So without further ado, I picked Naz. - Okay. - You actually, I felt
like in the first round, I like immediately was like
there's chemistry there and then I thought that there was like some stops and starts when you met, but. - For me it was between London and Naz. - That was wild. I mean I felt like we
had a good connection. We have like the same vibes
in that like long term. Like I kind of get the
lifestyle you're going towards which is really cool. Thanks for picking me. - What do I do now? - Do we like fight to the death? I'm kidding. - [Producer] It seems like
even though Simone didn't pick the exact person, she
was really, really close. - Yes, I'd say like, like 97% accurate. She's great, great at what she does. I'm happy she was here with me and she made this process a lot easier. - It's like such a joy that I've found myself in this position and I think that matchmaking is the future and dating apps are lovely and there's nothing wrong with them, but I'm all for like the return to analog. So I'm proud to be in
that space in this time. - [Producer] Would you be interested in going on a first date
with either Naz or London? - 1000 million percent, yes. But TBD, I don't know if I should do both or if I should do one. We're getting brunch later. Brunch as a group. Group date, fun too. So maybe I'll keep analyzing.
