Rethink Dating: Coffee Dates to Real Connections

In this episode, Jojo discusses the complexities of modern dating, emphasizing the importance of genuine connection over flashy displays. She shares insights from her conversations with friends about dating expectations, the impact of ego, and the need for both parties to engage meaningfully. Jojo advocates for intentional dating practices, such as starting with low-pressure coffee dates instead of extravagant dinners, to foster authentic connections and set healthy boundaries.

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Transcript

Jojo (00:06.99)
Welcome back to another episode of Inside Out. I'm your host JoJo and this is where we'll navigate the mess together. That is mental, emotional, and spiritual. Let's get into it.

Jojo (00:27.342)
Well, hello and welcome back. This week I wanted to talk about dating. I was having a conversation with a friend of mine and I was kind of coaching him in a way on dating from the female lens, but as a man. And he was in town in New York and he was taking this girl out on a date and he was so excited, but there was like not a grounded energy of

a way that he wanted to really make this date happen or, you know, make sure the experience was a good one. And it was very much from like his perspective and his lens of ego. And I get it. We all have an ego, but through this conversation, he really dropped in to really how dating and how people show up to dates really does affect the outcome of our relationships.

And this is a first date, he'd never met this girl before, but I wanted to talk about this because I think all of us females have guy friends in our lives. And we kind of had these conversations with them and we're like, this is what we want, but what we get is so drastically different than what we're actually looking for. We don't care about, I mean, okay, I'm talking about myself here, but a majority of women do not care.

about the most expensive restaurant that you take us to, this super flashy date, or spending a ton of money on us when we haven't really done anything to deserve it yet. Like, yeah, we can always argue, we deserve to be treated well. Of course we do. But I'm saying like as a first date, that's not necessarily the highest priority. We're actually seeing like if there's a connection and a lot of guys want to just flash and flaunt and be

you know, the hottest shot in the room. And so I was talking to my friend about this and I was like, all we want is to be seen, listened to. We don't want it to be all about you. Let me use a name for my friend. We don't want it to be the Jack show. It's not the Jack show. We don't want to walk into a date with a man and it being like,

Jojo (02:52.654)
They're just bragging about their job, what they do, and there's like no questions. We want to be asked questions. We want to feel like you're investing in us. We don't want you to just ask us a question and then flip the script back on yourself. I mean, I'll be even with my guy friends and I'll be talking about something and all of a sudden it's like right back to them, which is fine. When we're dating, it's two people. And typically, I mean, this goes both ways, but...

There's a misalignment when one person is just over dominating with trying to impress the other. And typically I have to say like it is the man because they want to get us a car and take us to dinner and do all the nice things and take us to drinks after and kind of have this like lineup of like, my God, I'm going to knock her socks off. And it's again, it's very much about the me, me, me mentality of like, how am I showing up from the guy's perspective? We don't care. Like,

Truly, know, again, women might want that to a certain extent and maybe there is a higher percentage of women out there that are like, no, I want you to like get me a car and take me to the nicest place and all that stuff. that, okay, that's totally fine. But a majority of us just want to see if there's a connection to see, this someone I can talk to? Is this someone that I can like build something with? Back to my relationships episode. Is this someone I can plant a seed with and really have a healthy

plant grow? Because rarely are you going to sit across the table from someone who's just flaunting and bragging and has an ego the size of the Empire State Building. And you're like, what? just like, this was all about them. And I feel so unseen. I feel so unheard. They didn't even get to know me. It was like, could have been anyone across the table from them. They probably just would have done the same thing. How many guys actually drop in and are like, no, I want to get to know you.

or like actually like put in the work to really ask us questions. I've been on so many dates where I'm like, I literally could have been anybody. I could have been your therapist. I felt like your therapist actually. And it's just constantly about them. And it's actually made me personally just not be interested in talking to that person again. Not because I have the ego of like, well, I need to be seen, but just like,

Jojo (05:13.528)
There's no give and take. There's no equal reciprocity. There's no room for me here. A relationship's two people. A conversation's typically two people. You're not just talking. This isn't a podcast when you're on a date. You're not just like talking into a microphone with no feedback. There's someone sitting across from you. And also personally, and I have polled my friends, we don't want to go to dinner on the first date. That's a lot of pressure. And also like, we don't know what your intentions are. If I...

get a coffee with you and take a stroll, I have way more ability to see if this is a good investment of my time for an hour, an hour and a half, three hours the rest of my evening. There's so much pressure that's taken off and there's no financial commitment or expectation on either side because if you just get coffee, that's $5 a little stroll under an hour and you just see if there's a

energy, if there's a vibe, if you guys click. I can't tell you how many of my guy friends are like, I am so over dating because it's such a financial commitment when they're just taking out girl after girl after girl and some women actually are just wanting a free dinner and that's totally fine. But that gives the women who are truly looking to build something with someone an unfair advantage because maybe a man gets to the date and they

are kind of jaded because they're like, that she just is going to expect me to pay. She's not going to pull her wallet. She's not going to, you know, it's all like all the financial burden and responsibilities on me. And I don't know, I might never see her again. This one friend I was talking to was like, yeah, usually like there's a first and a second date, but it doesn't really go further than that. And I was like, why? I'm like, let's get into and break down. Why? Why is there not a second date?

And he was like, well, I want to like take her here and go like to like a really nice restaurant. And then the night goes on and it's like really fun. And, you know, I'm just trying to show her a good time. And then maybe the next day I take her to like a sporting event, like the U S open or a Yankees playoff game. And I'm automatically just sitting there like, there's, there's no room for this to go somewhere. You started at the top. There's only room to fall.

Jojo (07:30.698)
Once a woman is getting all of that straight off the bat without really having like earned it's the wrong word. Cause again, we do deserve this. Everyone deserves to be treated really well. Of course. It's not what I'm saying here, but if, if that's the start, we're going to just expect it to keep going up, up, up. And there's no room for it to level out and be normal. If you start at coffee, there's so much more room for anything else. Literally coffee than maybe seeing a movie.

going bowling, get more active, take a hike, then go to a sporting event, then go to a nice dinner, comedy show, Broadway. There's more to build on, but if you're automatically just doing the most fun thing right away at the top, it's like, so where's this going to go? You, kind of already got everything I wanted. And maybe that's why some girls are like, okay, well, if someone's going to treat me like that on the first date, someone can treat me better. And I, I do want to play both sides on this because I think it's, it's so tough and you hear about it in every city. I friends,

all over and it's like, my gosh, Scottsdale is the worst city to date in. my gosh, LA is the worst city to date in. London's the worst city to date in. Chicago is the worst city to date in. New York is the worst. I mean, we get it. Everywhere's the worst. But is it actually the worst or are people just showing up kind of not in a realistic way on these dates? Like you're showing your best foot forward. That's cool. You should be polite. You should be a gentleman. You should be chivalrous. You should show you care.

you should show that you're there's like investment in this person. But I think there's a way to do this and kind of dial it back a bit so that we're not burnt out on either end. We're not burnt out on the giving or the receiving end. Cause if a man is constantly again, paying for the dinners and doing these expensive extravagant dates, the right woman can come along, but she's going to just be treated probably the same way. And he's going to be resentful of that.

maybe unknowingly because he's done it so much. think there's so many expectations that come into dating when it's just two people meeting for the first time, having a coffee and taking a walk is probably the most grounded way to see how you communicate. Is there a conversation here? Is it one person just constantly doing the Jack show or I mean, women can also do the

Jojo (09:47.778)
the Jojo show, you know, we can sit here and be like, my God, I did this and I did that. And like, it can be all about us, but no one is actually who wants to see if there's a connection between you two going to look at that be like, yeah, I'm just going to be in her shadow the whole time. No, we all want to be seen. We all want a voice. We all want to be heard. We all want to be respected and appreciated, but that doesn't happen if it's one sided on these dates. There's no room for growth. It has to be.

a natural progression in a totally unnatural world of dating. Riddle me that. So I was talking to my friend and I told Jack, okay, well like he wanted to actually go pick this girl up from her apartment in an Uber. And I was like, all right, too much, way too much. You've never met her before. Like we need to dial it back. If you want to send her a car, send her a car. Fine. You know, he sends her a car. They meet at the restaurant. That's amazing. But I was like, even just in the conversation that I'm having with you right now,

everything that I'm saying to you, you're turning it back on you and you're like making it about you. He asked me a question about like my career and I started talking about it. He's like, yeah, I'm like trying to find a new job. And I was like, Jack, you're doing it again. You have to let her talk. You have to let me talk. Like you need to not just like keep making the conversation go back to you. You need to drop in. You need to listen to her, really listen to her because if you're not interested in anything she has to say, why are you out with her? There's so much.

flashiness that happens in dating today. Again, I think it's just, it's so tough because the majority of us, we just want a real connection and the other parts of us just want a fun night. Whether people want to admit it or not, we all want to find a real connection with someone. We all want to find our person. It might not be right now, but then get real with yourself about that because if you are going on these dates, giving a false sense of, want a relationship and then you're doing all these things and

giving yourself that feedback loop of, it's so expensive to date in New York. I always have to pay. Women just want a free dinner. And you're not actually wanting to be dating in the first place. You're setting yourself up for failure. But if you truly want to build a connection with someone, why not find out if that person is actually someone you want to build a connection with by not spending $400 at dinner or on an entire night and spending $5.

Jojo (12:14.006)
on her latte and 40 minutes on a walk. And just seeing if there's any sort of interest connection or anything, because you'll know straight off the bat if that girl is looking for your money or if there's actually something stronger, deeper there. You know the show The Bachelorette, these people go on insane dates. Their first date is like a helicopter ride around some beautiful island or paragliding, but it's the top. Of course, that's the best date you've ever had. It's the top of the totem pole.

for experiences. Same thing if you take a girl to a really nice fancy dinner like an omakase or a chef's table, like pairing with wine and it's going to be so much fun because you're doing such a fun experience together. That's not a reflection of life. That's not a reflection of a real relationship. And that's not also a reflection of an authentic connection. You can connect with anybody doing something fun. You guys are having a shared experience. Of course it's going to be fun.

Are you able to build a real connection or have just as much fun with someone walking down the street, drinking a coffee? And maybe that's where we get stuck. Maybe what really sets us apart from finding someone is the resentment and the expectation instead of the connection. So just to offer a little bit of advice, date different, go on a walk, get a coffee, get an ice cream. If you don't drink caffeine, get a tea. I don't know. Do something different. Don't.

sit down at a restaurant or do something super fun and out there. Like just take a walk and get to know the person. See if there's like any sort of anything there. Then if you even like their company, cause you can like someone's company if you're doing something fun, it's easy. And if you're having a few drinks and like some social lubrication to like, you know, ease it up, get the nerves out, you can kind of gaslight yourself into thinking that this is a connection when you probably don't have anything in common.

And then you're just perpetuating more and more dates, spending more and more money, investing more and more time and money into this person when you could have just gone on one date, one coffee stroll and seen it's a yes or a no. And also from the female perspective, we can see if it's a yes or a no. Are you guys talking about yourself the whole time? Is there any room for me here? Are you interested in me at all? Men don't ask us questions. Ask us questions. I feel like us women, we want to dig into you a lot. like...

Jojo (14:40.194)
We asked you guys so many questions because we're so used to it because otherwise it's going to be silent. Men, you guys don't ask us enough questions. I'm sure there are men out there that ask very good questions and there are. I've met you, I know you guys, you exist. But I'm talking about from the conversations I've had with people in my life, from research I've done on this, from podcasts, from just the general population. There's two sides. Women expect that a man will pay for them on their first date and men, women expect

not to be asked any questions or that you're going to like try something on us or that you only want one thing. And it feeds that perpetual cycle of why people just don't connect authentically anymore. Again, we see something pretty. We see something that has money. We want to just take, take, take. We're not actually showing up to just see, but also don't date if you don't want to like really date or just date unintentionally and then just don't care about anything I'm saying and do whatever you want to do.

this episode does not apply to you. But if you're really looking to date intentionally and get to know someone intentionally, men ask some questions and women stop expecting so much. Just see if this is a dude that you want to like come home to after a long day and feel like you can vent about your day and that they're just going to hold space for you. We don't need someone to fix our problems. Sometimes we don't even need anything. We just need someone to listen. Men listen, women also listen. This honestly,

I don't even know I'm saying men and women. This just applies to both. So let's navigate this mess mentally. Dropping in, being present, asking the right questions, not having expectations of what it should be or how they should be, and just really getting to know the person on the other side of not the table, the sidewalk. Emotionally, do you connect? Is there a give and take? Are you guys able to talk about stuff? Or is it just one person talking the entire time? Spiritually, if you're being more cognizant,

of how you do show up to dates and really what that looks like and being honest with yourself on an emotional level, you're spiritually just going to change the trajectory of your dating. You're going to be more dropped in. You're going be more present. You're going to be more grounded, more available, more honest, more vulnerable. And if you are looking for a partner, it's probably going to be a lot easier because you're going to see clearer who you want to invest your time in, where you want to invest your money.

Jojo (17:05.174)
and with whom, and it's going to be way more fulfilling, that's for sure. So while dating can be such a mess, so crazy, if you really pull it apart and slow down, it can get a lot more simple. New York's tough, Chicago's tough, LA is tough, Scottsdale's tough, I'm sure Miami's tough. I mean, I can keep going, but I think we make it harder on ourselves because we assume where the other person is coming from.

And then we try to meet their expectations without just getting in touch with where we're at, what we truly want, and then holding ourselves to that boundary and that standard. Because when someone's opposing us, sitting across that table, standing across that sidewalk, on that date with us, it's so easy to go back into the same repetitive things that we've always done. Flashy, talk about myself, spend the money, do the fun thing, be the best guy. Our egos get huge. Same with the girls, wear that cute dress.

dress up to the nines, expect that we're going to be treated like a queen. We're just setting ourselves up for absolute failure. Take a beat, get a coffee. If you don't know how to change your dating cycles and someone's like, I'd love to take you to dinner. Be like, it sounds really nice. Maybe eventually, but let's meet for a coffee first. Adjust your boundaries, take back your power. And also men, your dating pool might get a lot smaller, but if you want to be more intentional and you're like,

I'd love to get a coffee with you." And the girl's like, no, I only do dinner on the first date. Well, okay. Maybe it's someone you really want to take out, but do you really want to go back into that same cycle? So hold yourself to a higher standard. Hold yourself to that boundary. Someone's going to try to cross it, but it's up to you to instill it. You're going to be tested. Choose yourself, choose what you want, choose what you're looking for, and then implement it. Let's make dating a little easier on all of us. We could all use a break and we could all...

really use a lot less pressure when it comes to how we show up on these dates. And let's like really just be ourselves and not try to project or perform or be a certain version of ourselves. Don't wear your cutest outfit. Don't spend the most money. Just put on a cute pair of jeans and a top and maybe don't blow your hair out. Just be natural. Cause again, if you're looking to build something with someone, your partner is going to see you eventually. So stop putting on a show.

Jojo (19:28.014)
All right, guys, thank you for going Inside Out with me this week. Don't forget to share this with a friend, especially this episode with a friend and a guy friend and a girlfriend. Pass it along. Subscribe on Spotify, follow on Instagram at underscore inside out dot podcast, and I will see you all next week. Have a good one. Bye.