Pops and Son Conversations
Join US Air Force Veteran, Presidential Achievement Award Recipient, author, philanthropist, and social media influencer, Rob Malloy, and his son, author and model, Javan Anderson, as they navigate the generation gap with humor and heart.
On this podcast, Rob and Javan tackle a wide range of topics – from life lessons and fatherhood to current events and pop culture – offering a unique blend of old-school wisdom and new-school perspectives. Expect lively debates, unexpected insights, and plenty of laughs along the way.
Tune in to Pops and Son Conversations and discover:
- Candid conversations: Rob and Javan share their honest thoughts and experiences, providing a refreshing take on intergenerational relationships.
- Diverse perspectives: Hear how Rob's traditional values intersect with Javan's modern outlook, creating dynamic and engaging discussions.
- Humor and heart: Enjoy a show that's both entertaining and thought-provoking, leaving you with a smile and something to ponder.
Subscribe now and join the conversation!
Pops and Son Conversations
Romance or Rebuilding: Can You Truly Afford to Date Right Now?
"Romance or rebuilding?" That's the crucial question facing many men today when it comes to dating. As we explore during Financial Literacy Month, dating isn't just about having money—it's about having the complete package of resources: financial stability, emotional availability, time, energy, and creative effort.
The pressure on men to provide memorable experiences hasn't changed in centuries, but what if you're in a rebuilding phase of life? We dive deep into this reality check, exploring how transparency about where you stand financially and emotionally isn't a weakness but a strength. Authenticity attracts the right partner who appreciates your journey.
You don't need to be wealthy to create meaningful connections. Some of the most memorable dates cost very little—painting in the park, a thoughtful conversation over coffee, or exploring a local neighborhood. What matters most is alignment—finding someone whose expectations and values match your current position in life, creating space for growth together.
We share personal stories about expensive restaurant disasters and surprising revelations about what really impresses potential partners. The difference between flexing (which rarely works) and intentional dating (which builds real connection) becomes clear as we explore dating psychology. Even married men need to hear this—are you still dating your spouse with the same enthusiasm you once showed?
This honest, unfiltered conversation goes beyond typical dating advice, offering practical wisdom for men at every stage of life. Whether you're rebuilding or ready for romance, understanding the true affordability of dating—in all its dimensions—is the first step toward authentic relationships. Join us for this essential discussion that reframes how men approach dating in today's complex world.
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Welcome to another episode of Pops and Son Conversations. It is your favorite Silver Fox, Rob Malloy.
Speaker 2:And it's your favorite poet, Mr Check Three Times.
Speaker 1:Yeah, welcome to April. It is the second quarter. Jay, how are you feeling about the second quarter?
Speaker 2:You know I'm feeling pumped up, I'm feeling ready, I'm feeling motivated. You know, yeah, it's that time, it's that season.
Speaker 1:It's a good season, man, it's a good season, so that means we got to bring some flavor. So it's financial literacy month. A lot of people didn't know that. I did not know that we had to get some help to let us know that. I've never heard of and unfortunately I didn't know that there was a financial literacy month, did you, jay?
Speaker 2:I had no idea. Yeah, I'm not. I'm not afraid to admit it. I did not know um, but I know now, so you know progress progress, progress, all right.
Speaker 1:So, um, we want to just really kind of jump in with the gratitude we thank you guys for, you know, support for not only listening to our podcast and celebrating and supporting our brand with us, but also just being a great inspiration, and folks keep telling us, you know, they're excited about what we're doing, what we're bringing. That is very needed, and man, we're just thankful needed. And man, uh, we're just thankful. Jay, I didn't know that we was going to get this amount of support um, internationally as well as worldwide.
Speaker 2:yeah, yeah, it's, it's. You know, it's been amazing just outpouring from, you know, people showing love, uh, across the internet and in real life. You know, I meet people and they tell me, uh, you know, man, I love what you and your dad got going on, I love the podcast and everything. So, yeah, it's definitely something special and it makes you feel good because it's like, all right, I know that this is what needs to be happening right now, like this is. This is this is something special, mm hmm, yeah, it has been special.
Speaker 1:So again, thank you guys for your support. Uh, thank you, you know, for your wonderful energy and good vibes. Man, all that, all that makes a difference. You know, even even the ones that do a behind closed doors. Right, you don't comment, you don't like, you don't share, but you know, you'll jump in there, maybe in the DMs or maybe a text messages, and talk about how proud you are. We, we appreciate that too. It's OK. Yes, indeed, yeah, All love is appreciated and welcome. So, that being said, hey, let's jump in. With it being financial literacy month, I think we have to talk about money money, money, money.
Speaker 1:we have to talk about money, money, money, money. We got to talk about money. So, you know, being that this is a pops and son, a father and son, a dad and his protege, I think we should just kind of jump into dating.
Speaker 2:Yeah.
Speaker 1:Let's talk about. You know, can you afford to date, mm, hmm yeah. Let's talk about you know, can you afford to date, mm, hmm yeah. And that's as a young man, as a grown man, that's whatever stage you are in life, you know, can you afford to date? So I think we should start out by just kind of define, defining afford, right, because it's not always about money, it's not always about the cash.
Speaker 2:I mean it is, but it ain't. It is, but it ain't.
Speaker 1:It's also about you know. You got to think about investing time. You know energy and you know one of the favorite words the ladies like to use man, you have to be emotional, emotionally available.
Speaker 2:Exactly, they love that word man, emotionally available. Exactly, they love that word man.
Speaker 1:Emotionally available in emotional intelligence. Those are the two buzzwords that our sisters around the world love utilizing man.
Speaker 2:Yeah, so this is how I feel about it. This is like it's such a great topic because there's always talks about, you know, the man's role in dating and we already know how that go. But at the end of the day, dating isn't free, all right. So I'm not just talking about splitting the check. Like you said. It's time, energy, your emotional maturity, but it's money too. It's money too. You can't leave out the money. So this is what it is. If your pockets hurt every time you go out or you're trying to take somebody out, you know, or you got to move some money over here, like listen, you might need to ask yourself this hard question. I know you're gonna like this part is this the season for romance or the season for rebuilding? Yeah, I know you like that, so listen that was right off the top jay that's off the top.
Speaker 1:Okay, okay, romance or rebuilding is boiling tonight.
Speaker 2:Yeah, because I know. You know we've had conversations and you've talked about how you know there could be a point in a man's life where he's going through a stage of rebuilding, Right? So I think that once you identify where you are at as a man, you just make it easy on yourself, right? You don't need to be out here trying to spend hundreds of dollars on dates and you ain't got it like that. That's just the real, and it's no shame in admitting that. You know it's no shame, and I think that you're even more of a man by saying, like yo, you know, let me not even try to fake it or flex, and let me just go ahead and be straight up with you. I ain't got the money like that. Now, there's a flip side to that too, though, Pops, Because you know people think you have to be a millionaire to date. That's not true either. So you know you ain't gotta flex. You could do something that expresses your creativity, right? Uh, women like that.
Speaker 2:They like when men are creative, they like when you're honest and present yeah but this is another part too, and I know I'm going on, but keep going I like the man.
Speaker 2:The main thing about it is and I know you're going to like this too, because we didn't listen Pops, I've been picking up the gems you've been dropping, you just didn't know. So, listen, when it comes to the can you afford to date the question, it's one word that pops in my brain Alignment, okay, alignment, okay. A lot of guys, I think, we trip up when we want to. We maybe, we want to attain, or maybe we want to, uh, try to date women that aren't really aligned with us and where we are at that point in our life yeah so, yeah, we know dating costs money and for men, traditionally, the pressure is on us to provide the experience.
Speaker 2:That's not going to change. It ain't changed in 100 years. I don't think that it's going to change anytime soon. It shouldn't, and I don't think it should. I think that I fully accept that responsibility and I like to be able to provide that for the woman I'm interested in. It boosts my ego up a little bit. I'll admit that too, but I ain't mad at that. I don't think she should be mad at that either. Let me get my ego on a little bit.
Speaker 2:I know you like this restaurant, I know you like the whip, but nah. So I think that it's really about mindset and alignment and just really recognizing where you are in your state of life. So when you're saying, can you afford today, like you said, we do have to define that right. So are you emotionally mature? Are you available enough right now? Today, can you afford to expend the emotions that it's going to take? Okay, can you afford the money that it's going to take? You can't leave the money out. The money is there. Can you afford the energy? Can you afford the, the, the, the honesty and the time of, uh, um, really talking to somebody and getting to know somebody, because a lot of guys just go in thinking I got the, I got the bread, I got the money.
Speaker 1:Yeah.
Speaker 2:But you could fall into a downward spiral and back to the millionaire point. Right, you got even millionaires that might not even have successful dating lives, because, yeah, they can afford the money, but they're lacking in the emotional availability and maturity, they're lacking in the energy, or they may even be lacking in the creativity and effort too, because the effort is another piece of the puzzle. I like it the effort is another piece of the puzzle.
Speaker 1:Yeah, you dropped a lot of gems. Take a deep breath. You did your thing, man. That was very powerful.
Speaker 1:Though, jay, I'm glad that you mentioned everything, I won't even add too much to it, but one thing that you did mention you mentioned you have to really be transparent in where you're at in your journey in life. You have to really be transparent and where you're at in your journey in life, because dating may not be priority, right? Uh, like you mentioned, uh, rebuilding. I think anything that has to do with personal growth and development should supersede anything else going on, because you have to. You have to at least be working to be the best version of yourself and have that understanding of what it takes.
Speaker 1:Now I will be biased. I do think that men have a have more obstacles, mainly because you know we're looked at as leaders and providers and protectors, and so when you start talking about money, energy, emotionally available, I think those are going to weigh a little bit more on on us men, because we do have to create the experience. There's a lot of expectations when it comes to dating. Let's just be real about it. Even if a woman finds a guy interesting and wants to get to know him, she still wants him to ask her out on a date. I like you, but you ask me out.
Speaker 2:Exactly.
Speaker 1:That's something I'm not even going to get into that, because I don't want to talk about that too much on here.
Speaker 1:I want to make sure we start talking about being able to afford to date.
Speaker 1:Now, listeners, you know that our podcast is Pops and Son, so we're talking about men.
Speaker 1:We're talking about men, can we afford to date?
Speaker 1:So you're off the hook in terms of having to ask this question, but, but we know that you feel like it's an important question because historically, you know, quote unquote men shouldn't be dating if they're broke, right, and I think that that really goes directly in terms of money, right, and the thing about it is, if a man doesn't have a whole bunch of money and he can, you know, sustain his own lifestyle and he's self-sufficient, you know, there's really no reason why he can't date.
Speaker 1:He does not have to have, like you mentioned, a million dollars in the bank, right, and the great part about it is it really also allows him to find someone and pursue someone that understands that, that understands what rebuilding is, that understands what a journey is, because everybody goes through it. I don't care how much money you have. You still went through some type of physical sickness at one point in your life, some emotional turmoil, and then you had some low energy and depression in your life. So you got 200,000 in your savings and 500,000 in your checking, but you are emotionally unavailable, should you be able, to date.
Speaker 2:Right.
Speaker 1:Is that, you know, a wise decision to move forward. And my answer is you know, as long as you understand the that particular journey, if you understand that the person that finds you interesting is going to have to be some transparency, why not? You know, we're just talking about money sometimes and people go through money issues, especially even when it comes to, you know, business owners and entrepreneurs and millionaires and things like that. You have to move money around, you have to invest your funds. Sometimes money is tied up depending on what you have going on and, to be honest, sometimes you just want to do something simple to see if she gets you. Sometimes you just want to do something simple to see if she gets you. Like, who's not going to have a good time when it's a seven star restaurant and you on the top of the skyline or you're on a boat or a yacht with your friends? How are you not going to have a good time?
Speaker 2:It's hard not to Right.
Speaker 1:Right, but what about when stuff is going on in life? Or what about you having some challenges and you doing some transitioning and things like that? Can you date then? Can you separate that and really just to get to know the person? Because you want somebody that understands that you're going to need some support and the reciprocity is going to be key and so let's not pretend like it's always gravy.
Speaker 1:No it's not always gravy. So, realistically, man, you want somebody who's going to be real with you, and that's what I would add when we start talking about. Can you actually afford to date? So you take all things in consideration. But man please, man please, about the money thing, like, let me say this and then we'll move on. You know I always got stories right. So I remember two instances, man. I'll say one tried to impress this young lady and I'll be honest with you, this was a minute ago. I ain't like that, no more. I'm beyond that. I remember I was trying to take her to this nice restaurant and stuff like that. Now, could I afford it? Yeah, I can afford it, but it's going to put a dent in your pocket.
Speaker 1:I don't care if it's $250, $200, $300, or gonna put a dent in your pocket. I don't care if it's 250, 200, 300 or 75 dollars. Sometimes when you got stuff going on, that's gonna put a dent in your situation. So, uh, so we went out to this restaurant. Now here's the first thing the food wasn't that good. You know, the food wasn't that good. It was like, uh, and all the stuff was was weird food. You know. I mean, it was like like weird food. You know, when you start adding the truffles, oh man and all this and the snail man.
Speaker 1:It was just weird food fancy weird right. So you know. Afterwards she was like um, I'm not trying to be funny, but you know we could have went and got some wings. Wow, a lesson learned I was like what I thought she was a bougie chick man.
Speaker 1:She said you know, I like to eat, so I want to eat food that I like now, not experiment. Right, I was like you know what? Why you ain't say anything before you. You know, while looking at the menu, because I'll walk out, I'll walk out a restaurant man, I am not obligated to stay there, but, uh, you know, lesson learned, that was definitely a lesson learned. And then the other experience was um, you know, I found out that a lot of times women do like simplicity, so it doesn't have to be a well-known five, six, seven star.
Speaker 1:But you know it could be something to where the ambiance is really cool and you know as long as the food is good. But you know really the ambiance where you can talk, you know even maybe get some dancing in. Like just a whole high energy experience will supersede a super fancy situation where you got to be stiff anyway.
Speaker 2:Yeah.
Speaker 1:You know you're looking crazy. You can't really laugh. Folk don't look at you crazy if you're laughing.
Speaker 2:Yeah, you already feeling out of place a little bit oh man.
Speaker 1:Well, you know, in terms of being able to do what you want to do to make the best of the situation, yeah, yeah, so, yeah, man, so I just, I just learn, create the experience, you know, have some conversation and really find out. You know what that person's vibe is, because a lot of times they'll tell you. You know it's cool, we can go to the steakhouse sometimes, but really sometimes I just want to go somewhere where you know you can walk. You know she might want a funnel cake, you know.
Speaker 2:Nothing wrong with that.
Speaker 1:Things or something like that, but just walk and talk and hang out under some beautiful lights and scenery.
Speaker 2:Like the movies man.
Speaker 1:Just like it man.
Speaker 2:Like scenery, like the movies, man, just like it. Man, just like I do, like the movies they don't always do that, you know. Spend all them hundreds on the dates, like you. Hey, they'll be out there feeding the uh, the ducks and stuff, throwing bread at them yeah then, it's different than what you know know the average guy would do.
Speaker 1:The average guy's a dinner and a movie all day long, right? So imagine a woman you know doing that, uh, from 21 to 41, like that's all the brothers doing 10 in the morning in the movie. You know so, uh, you know, sometimes you got the the free to low cost dates walks, and you know cooking class and painting classes oh, that's good.
Speaker 2:Yeah, that's real good.
Speaker 2:You know making prizes and candles come on, yeah think outside the box, even take it a step further and, just, you know, just go and get the materials, Like, hey, I got a little setup over here at the park, I got some canvas, I bought the paint, everything that's a date right there. That is Low cost, You're not spending hundreds or whatever the case may be. And number one, which should be priority over everything, is the experience. I think if you just work toward having a good experience on a date, then the money you forget about the money, right? Don't put so much focus on it. So it's really a lot of different layers when you talk about can you afford a date, and I like how you mentioned.
Speaker 2:You know, traditionally this question is for the men and we don't want to get to the other side of it with dating. If being broken dating, I know where you were going, but you know there's other ways to tackle it right. So you shouldn't feel discouraged if and I know I mentioned about the timing of it, the timing and if you need to be, but that's I still think that's also a part like, honestly, if you don't think that, uh, um, you in that position, it's okay to also say you know what? Let me rebuild right now. Yeah, you know, but don't also just don't think that today you need to have money. That's not the case. I want to make that part clear too, because there's plenty of ways to to, you know, to get around that and then you just find a woman.
Speaker 2:That's, that's okay with it. You know, look for what is, you know, uh, uh, align with what you can do, and what you have going on is people that are falling in love, and you know they both aren't the richest you know, and it goes all across the board. So, yeah, I think that you know it's levels to dating, but that's just what that means. You know it's levels to it. You just got to figure out what level you're on.
Speaker 1:That's a fact and you have to also take in consideration as we continue to talk about this, this topic. You know, can you afford to date? And we're asking each other, we're asking all men out here, all fathers, all sons, you know, even if you marry me, can you afford to date? Are you dating your wife? Are you dating your wife? That's a good one. Are you? Are you taking the wife out, just like you you did, or even more, when you guys was, when you was courting her?
Speaker 1:Now, that's one thing that is universal, because sometimes people say, well, what you single guys got to say about us married folk, mind your business, mind your business.
Speaker 1:But you know, when you look at it more so it's, uh, it's universal principles, man, that we have to take in consideration. So I think that that's super cool, but but but again, you know, you have to look at are you actually trying to build something with that person? You know, are you or you guys just vibe and like is it a casual, casual situation? Or is it somebody that you are consistently getting to know, someone that you are looking to transition from dating to courting? And so I think all those things will definitely be taken in consideration, jay. So let me ask you this definitely be taken in consideration, jay. So let me ask you this what do you feel when it comes to a person that you have to ask him? Are you trying to impress someone? Are you trying to connect with them? What do you think is the big difference between somebody just trying to flex or someone who is trying to be more intentional with their efforts?
Speaker 2:just trying to flex, or someone who is trying to be more intentional with their efforts, right, yeah, so I think, um, I think the person that's trying to flex, um, I think that you know there may be uh, you know it, it might be some things going on. You know on the inside that they need to to figure out because, at the end of the day, the intentionality part about it is really the crux of dating. Right, you want to be, you know, working towards something, unless you already have, you know, stated like there's different forms of dating. Right, you could be dating casually. You might've just got out something. You don't want to get too serious too soon, but you want companionship. You still want the romance, like, you don't want to just be lonely all the time. So that's cool too, you know.
Speaker 2:But I think there's just a hint of you know the the flexing part about it is a little misguided, right, you don't, because you only going to drain yourself, you know you're, you're only fooling yourself when you are, you know, kind of putting up this facade and maybe you're doing it to try to to get women that you feel like you weren't, uh you wouldn't typically be able to get if you weren't flexing like you are. But that just goes to show, like we said, like you probably lacking some other things, because those same women, nine times out of ten and women will tell you like I'm not, the money don't impress me, money doesn't impress a lot of women, so you have to have something else, you have to have that creativity, you have to have that substance right. That's the word I'm looking for. So I think that the guys that are, you know, doing it, the flex, without really, you know, having good intentions behind it. They're just lacking substance, right, and that's probably what you need to figure out.
Speaker 2:Like you know, take some time to yourself, rebuild, you know, read a couple of books, you know, maybe look at some financial literacy courses, flip on this podcast. You know there's different things you could do to raise your levels Right. So, yeah, I think that's, that's the main difference to me.
Speaker 1:I like that. I do like that, and you know I feel like women set the standard. You know people talk about standard and tone all the time. But when I say women set the standard, what I mean is, you know she shares what her experiences are meaning for herself. So if she's a you know, a fancy, fancy mama, you know that's cool. I think that that's it's cool to be real, because if you don't know and then you get into a situation where you plan this date and stuff like that and she got the fake like she really likes it, but she doesn't, you know that that can be um a little off-putting in the long run because you know you didn't set that standard.
Speaker 1:I think both should set standard. But, uh, as men, as we continue to lead and you know you didn't set that standard, I think both should set standard. But as men, as we continue to lead, and you know I feel about leadership, the best way to lead is to serve, and so, as we become better leaders and listeners and having the ability to serve, I think that it also takes some listening and comprehending, so that we don't get caught up in a situation like me going to a super, super fancy restaurant. She won wings and ranch Right Like hey look, you know how many times we could have went out.
Speaker 2:This is about four or five days right.
Speaker 1:We could have had a little spot, man. We could have had a little mom and pop spot where they know us and they know you know, man. But you know I wasn't listening and you know I really thought that impressing a woman was getting, getting her or giving her everything that she asked for. In all actuality, it's just taking things in consideration because even if she wants this fancy experience, things like that, if that's not what I'm on at the time for whatever reason, then we're going to modify that, and if she don't understand modification, then she ain't the one for me.
Speaker 2:That's it.
Speaker 1:Right and and cause. It's going to take some, some compromise, some patience and understanding on both parties, because we don't know each other and the whole goal is to create something new. We take some things from you, we take some things from me and we create our own journey. It ain't okay, I'm going to do everything that you say because you like it that way. No, you had a guy that did that and where he, at Exactly you done, had the yes, did that, and where he at Exactly you done.
Speaker 1:Had the yes man before he ain't last.
Speaker 2:Fellas, don't fall into that trap, man. Don't be that guy. Do not be. That's a great point. Pops, I just want to say this as a man when you're dating, you should never have to change yourself, right? This isn't about becoming a different person, right. This is about finding a person that gels good with you and what you already have, your personality, what you bring to the table. If you chasing a woman, right, that's a no-go, right, because then you altering. Let me do like you say you become a yes man, you lose self, you lose purpose, you lose your, your, your, your, your guide, right, that compass is off at that point. So, yeah, you never. You, you never conform or try to mold yourself into into some different. I've never seen that work out.
Speaker 1:Yeah, man, Speaking of workout man, I think we worked out a good episode.
Speaker 2:Yeah, this was good.
Speaker 1:Yeah, it was solid. You know we may revisit it a little bit. Folks, you can always go to our social media and you can drop some. Hey, I listen to you. You podcast about. You know, can men afford to date? Drop some comments, drop some uh concerns, if you will, and in anything that you feel like would be um impactful to others, cause that's what we're here for. We want to get the message out from a perspective of a pops and son. So look, uh, we'll see you guys next episode. We appreciate you. Remember this is Financial Literacy Month of April, so it's your favorite still Fox, rob Malloy.
Speaker 2:That's right. Check three times, we are out.
Speaker 1:Out. See you next episode. Peace.
