Dating Over 50: 7 Telltale Signs of an insecure Man (Red Flags You Can’t Ignore!)

Why is it so important to recognize the signs of an insecure man — especially when dating over 50? Because insecurity doesn’t just disappear. It grows into jealousy, control, criticism, and emotional exhaustion. Robert Manni, host of Guy’s Guy Radio, unpacks 7 telltale signs of an insecure man — and why women need to spot these red flags before getting pulled into a draining relationship. Robert Manni ‪@RobertManni‬ is the author of The Guys’ Guy’s Guide to Love, a novel that has been recognized as “the man’s successor” to Sex and the City, and the host of Guy’s Guy Radio and TV.

Silke Schwarzkopf is the creator, executive producer, and host of 2nd Act TV, one of YouTube’s leading channels for candid conversations about dating, relationships, intimacy, and life after 50. Her journey to this work wasn’t planned—it was personal. Shortly after turning 50, Silke made the difficult decision to leave her 25-year marriage, close the production company she had co-owned for nearly two decades, and return to her Southern California roots to start over. Like millions of people navigating divorce, dating, and reinvention later in life, she found herself searching for guidance, encouragement, and authentic conversations that simply didn’t exist.

Drawing on her background in public relations and television production—and her own experiences of rebuilding happiness, finding love again, and creating a new career—Silke launched 2nd Act TV to help others navigate the challenges and opportunities of midlife. Today, she interviews leading experts on dating, relationships, intimacy, sexual health, and personal growth while never losing sight of what makes the channel unique: We’ve been there. We live what we bring you. Her message is one she hopes everyone remembers: it’s never too late to follow your heart, rediscover yourself, and create a life—and relationship—you truly love.

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If you’re the guy, do you do any of this stuff? And are you even aware that you’re doing it? And for women, it is important to recognize these signs
 [Music] Thank you so much for joining us again on Second Act TV
 Once again, I’m so happy to welcome back Robert Manny, the author of The Guys Guys Guide to Love and host of Guys Guys Radio and TV
 Robert, thank you for being here again
 Oh, my pleasure
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 Cheers
 Cheers
 Well, thank you for bringing that
 Get one, folks
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 I got the big one and it’s like it’s a terrific mug and I love using it on a daily basis
 Thank you
 And it does help support our channel
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 Keep the content coming
 Got some great content for you today
 At least I hope you think so
 We recently did a video with Trevor on seven signs of an insecure woman and why men need to be aware of this and avoid insecure women
 So, today we’re going to do just the opposite
 Got a lot of comments on, well, why don’t you do something about insecure men? Said, here we go
 What is it about insecure men and what what do women need to know? Why is this important? Why is it important? Well, listen, everybody’s insecure, particularly nowadays, but with uh dating, you know, supposed to be a fun sport, but it can be tough and a lot of women have their lists and uh and a lot of guys are like, I I’m not sure what is expected of me anymore
 How do I define myself? What are women really looking for? Do they need us? So, that creates an underlying insecurity just going into the dating parameters, if you will
 So, it’s it’s tough out there
 Also, the overarching issue is that it just it drains eventually can drain your insecurity or drain your confidence
 I mean, insecurities are a big thing to watch out for
 So, so let’s talk about some of the specific ones
 Some of the specific first one here, this is a great one
 Generalizing and and criticizing basically all women, lumping all women into a category, you know, all women this, all women that
 Well, I think too often we make generalizations without even knowing it just based on our conditioning where you say, “Oh, women are like this and guys are like that
” Nobody wants to be generalized
 A woman wants to feel special as she should be
 Particularly if you’re somebody you want to make an impression on and hopefully date
 You don’t want to just paint her as women and you’re all the same
 For me, that’s a huge red flag
 Anytime I hear all women or or for that matter from women, all men because you really you’re judging them through a filter of your own disappointments
 I mean, all women are not the same
 All men are not the same
 I think that’s a big signal to both sexes that if you hear that, hm, you may want to put a halt on this person
 And and if you if you do that, you know, why why are you saying that? Because it does not come across in in a good way
 whatsoever
 And we we hear it in the comments all the time
 I always find that interesting
 It’s like these are people who need you need to heal
 You need to get over this
 It It’s Yeah, you’re stuck
 You’re stuck somewhere
 Number two here, he one ups everything
 Now, that goes for both sides, too
 The oneuppers are just a pain in the butt
 Well, we all know somebody who’s I call them a topper
 And uh we know all know somebody who’s a topper and we all do it probably at sometimes and it’s a sign of insecurity frankly to be a topper because there’s no need for you to do that
 So if you’re a guy I would advise and suggest that you if a woman comes up with something like okay she’s run a marathon and you’ve run three you know you don’t have to like make her feel like she’s not up to your standard because you ran three and she ran one
 So, I would kind of if you have a topper thought in mind, hold it back and don’t put it out there
 Particularly if if it’s somebody new that you want to impress, that you want to hopefully date
 I would just know that you have that
 Okay, I’ve done three
 Check, check, check
 For me, she’s done one
 That’s great
 Most of the women you’re going to meet haven’t run a marathon
 So, if you’ve run three and she’s run one, you both run marathons
 That’s a good thing
 I know
 It always amazes me when somebody either either way, but I I think it’s especially insecure if men do it that, you know, you bring something up and right away, oh yeah, I was there
 I was there four weeks, you know? I mean, there there’s like something more that you did
 Saturday Night Live had a great character that did that
 That really showed how annoying how annoying this is
 That it’s funny your example because like I have run a marathon and then I’ve had guys Oh, yeah
 Well, me too
 I run
 So, you know, Well, let me ask you how many you ran versus versus Oh, that’s funny
 I don’t I didn’t know you did that
 I did
 Did Did you know I ran one? I did
 Yes
 Oh, all right
 Never mind
 Let me I don’t think our viewers care about that
 But yeah, the one upper just don’t you just you just come across as annoying
 Exactly
 You can dish it out, but you can’t take it
 Oh my god, do I not like people like that
 Go ahead
 Well, I actually find it I’d rather have somebody a woman make fun of me than criticize me and try to fix me
 uh because that just ne it seems to um from my own personal experience I’ve had a lot of situations where a woman will tell me always trying to improve me which I understand the intention but over time and I think a lot of guys would agree they just like okay in terms of dishing it out you know the less I can I can really dish it out and uh I can take it too but a lot of people they can’t dish it out they just don’t have the quips and uh and they can’t take it because they don’t like to be criticized or made fun of So, I think you have to really be careful when you’re dealing with different people, whether it’s a woman or a man, but particularly if it’s a guy, you don’t want to make fun of the woman you want to date
 You know, a big point here is that you can dish it out but not take it
 So, if you’re the one that likes to, you know, throw in one here or there and and I’m kind of like that, you know, Paul is like that
 But then, but we can take we can laugh at ourselves
 But it is that’s a huge red flag to me when somebody you know can dish it out but they can’t take it
 Huge sign of insecurity that will eventually I think become an issue in a relationship
 So absolutely there’s a lot of people who can’t take it and that that doesn’t mean they’re not they wouldn’t be a good partner and all of that
 You just need to be aware of it
 One that goes kind of along with that negging
 negging
 That’s a term I just recently learned, too
 But the example of negging, uh, you know, like, oh, you’re prettier
 You know, you’d be prettier if you smiled a lot more
 It’s it’s kind of passive aggressive
 And I think it goes I think it goes back to the book that was written about 10, 15 years ago
 The term negging came up, which was used as a kind of a maneuver, if you will, to make the woman feel offbalance, offkilter, so you could get the upper hand
 And it’s really is kind of a passive aggressive way like, hey, you’d look really great if you worked out
 You look great, but you look really great if you work worked out more or something
 So, the woman’s of course going to be insecure about that
 Like, oh, he thinks I’m out of shape or I’m not good enough
 So, I don’t know if that gets you anywhere
 If you’re a guy, you want to inspire her
 Maybe maybe what you’re saying is true, but there’s got to be a better way
 Like, how about let’s go to the gym together
 Be proactive
 Make it positive
 If you give that little dig that women are sharp, too
 They’re going to pick up on that
 And I made a generalization there, but I think it’s a positive one that women are pretty intuitive when it comes to like things that are guys are saying
 Well, yeah, some of us are, some of us aren’t perhaps, but that’s part of the problem is that we don’t want to see this or we we allow this to happen
 And negging
 Yeah
 those those passive aggressive comments that is not going anywhere good
 Again, a big big red sign
 And if you could point it out to them and you know what, you’re right
 I did do that
 I’m sorry
 That’s good
 But otherwise, that’s almost a narcissistic maneuver
 I think it’s interesting that that was used and maybe it still is used as a technique by some guys to make the woman feel to doubt herself
 Yes
 Why do you want to do that? This isn’t about, you know, dating and finding a partner isn’t about getting the upper hand
 It’s about common ground
 It’s about shared values
 It’s about enjoying each other
 So, I think you got to take a step back, guys, and say, “Okay, where am I coming from with this? Do I want to just get over on this woman, or do I want to be her friend and her partner and somebody that really relates to me?” Here, here’s another good one that we could probably talk about forever
 Height insecurities
 I mean, this is one that yeah, there’s some real insecurities and perhaps some valid I don’t know what
 Let’s talk about that
 Men who are insecure about their height
 Well, you know, it’s interesting, Silka, that studies have shown that taller guys actually in an aggregate make earn more than than shorter guys
 So, there’s also the fact that some women, not all, uh prefer a guy to be like at least six feet, let’s say
 And if you’re not quite six feet, then you’re, you know, you’ve got to check, you got to overcome that
 You got to get two checks to overcome that negative check
 And uh so a lot of guys, they’re they’re they’re they’ve been entrained by our culture to become insecure about their sight
 If you’re a guy and you’re 5’5, 56, unless you’re, you know, a big movie star, which a lot of them are
 A lot of the guys are on the shorter side, you you you know, you have an uphill battle for with with a lot of women, not all women
 I know they talk about now the short kings and all of that
 I don’t I don’t quite get where that’s coming from, but there’s a praise for shorter guys, which I think is good
 I’m kind of myself in the middle
 I’m like just 5’10”, so I wish I was 6’2 sometimes, but it is what it is
 And if you have a big enough personality, you can overcome your height
 And I I mean I don’t mean a big personality being obnoxious, but I mean being comfortable in your own skin
 And women will pick, in my opinion, women, and I’m generalizing again, will pick up on that self-confidence, not arrogance, but self-confidence and comfort in who you are
 And that’s a turnon regardless of your height
 I I 100% agree with everything you said
 You do think about that for some reason
 You know, taller is better than shorter
 And I don’t know, maybe it were wired that way for protection back in the caveman days
 I don’t know
 But yeah, that’s that’s a real a real thing
 However, if you have an insecurity about it, that just comes through, as you said, Robert, a much bigger turnoff than than anything else
 So, this is one to think about, you know, is a height insecurity really holding you back by the way that you’re handling it
 So, I don’t know
 Good for the women, too
 They just might say like, uh, I I dated a woman and she like she loved Daniel D
 Lewis
 I said, “Why?” She says, “He’s got really long fingers
” So, I’m thinking about all the lists that women that some people have, usually women, sorry, and all the obscure random things that are on there
 And how do you deal with that? So, if a woman has in her head, he’s got to be six feet to be the daddy of my baby, then what are you going to do about it? So, I think both women and men have to step back and say, okay, if I’m a woman, how do I what guys are going to meet my qualifications? If that’s those are my qualifications and if you’re a guy, if you’re dealing with a woman that way, what do you want to do to try to overcome it or just walk? It’s up to you
 But you might run into this that the point is for guys, you’re going to run into some of these pre-builtin prejudices and then you have to determine, do I want to do show her that I’m more than that or do you want to just say punt? Well, you definitely don’t want to show an insecurity about it because that that’s that’s the end the end then
 So, like like I said, it’s this is something we talk about for a long time because it does involve just looking at what your expectations are, whether they’re realistic or not, and throw those lists away
 That you know that we’ve talked about that at Nauseium as well
 Here, here’s another good one
 Making you feel too much meaning that you know, he says things like, “Oh, you know, I don’t know what you see in me
 I’m not good enough for you
 That you know at first that could come across as somewhat endearing but that that’s also not a good a good place to go
 I agree 100%
 Selfdeprecation I mean the world does enough to depreciate all of us
 Why why talk about that? Because it comes across to me also as kind of false and that what’s the agenda behind putting yourself down? Why why are you doing that? Does that make you more lovable or something? I don’t know
 I I don’t like it though and I don’t think it’s a turnon to women
 But I could be wrong
 Maybe some women like that
 I don’t know
 No, I don’t think any Well, let me talk for all women
 I’m starting to realize that the generalization is pretty easy to do
 We’re both doing it
 But that’s what Hey, listen
 You’re the woman
 I’m the guy on this show
 So the self-deprecating, yes, at first can be really funny
 And sometimes it is funny, but if you keep it on and on and on, you just get sick and tired of those people
 And it does it it absolutely shows an insecurity
 And it’s almost like you’re wanting you’re asking for some sort of positive feedback
 I I don’t know what you’re doing, but it it’s weak
 Yeah, it’s it’s it’s weak
 And don’t don’t don’t do that
 Finally here
 Don’t do that
 I love it
 What? Don’t do that
 I love that
 Okay
 Finally here
 This is This is fun, too
 Getting loud around other men or just in my I would say just people in general that sometimes you have men who are I mean they’re they just get loud for no for no reason
 I agree 100%
 I can tell you from I haven’t had alcohol in five years and I didn’t have an issue or anything
 I just stopped
 I don’t like going to bars or anything or with big crowds because in my opinion, alcohol, I’m witnessing it now, can fuel some loudness and it it just comes out of people that are repressed or whatever and they’re cutting loose
 So, I get it
 But there are people who are loud just to begin with and I find that incredibly annoying because what is it? It’s I need to be heard so I’m going to speak louder than other people
 And you know, so you have to say it is what it is
 If you’re a guy, I would turn down the volume a little bit
 If you really want to connect, you’re better off speaking on the getting in kind of matching the tone with the person you’re speaking with
 And if you’re a woman, you have to determine, wow, this guy’s pretty loud
 Do I want to listen to that all the time? Well, you’re in a mode of always proving yourself somehow
 And and and I know a few people like that
 you just want to tell them, you know, you would be so much more interesting if you just shut up
 I mean, there there’s to me it’s a huge turnoff when somebody just talks about themselves and especially if it’s in some kind of competitive way with with other men or other people in a room
 So, really think about that, you know, do you do this? Because it’s it it’s it has insecurity written all over it
 So, you know, again, why is this important? I I think this conversation today and and then I’ll throw it over to you is both, you know, if you’re the guy, do you do any of this stuff and are you even aware that you’re doing it? Because awareness is the first step to maybe make making it better
 And for women, it is important to recognize these signs because we do tend to get sucked into relationships where we then want to please and that’s that’s a bad thing too, people pleasing
 But insecure men can drain you
 absolutely drain you and and strip at your confidence
 So, I think that’s why this this is an important conversation
 Robert, I’ll throw it over you to close
 Real quick, one, if you’re a guy, just be yourself
 And uh that’s the because your yourself is going to come through ultimately, so might as well just be yourself from the beginning
 Secondly, I think we were both somewhat guilty of this is that we make generalizations
 I made generalizations about women
 You made some generalizations about women and guys as as I did
 So everybody does that to a certain extent
 So I think we all need to be mindful that we don’t want to paint everybody with the same brush based on their their sex
 So we’re learning and we learned here during this conversation
 So I think it’s all good
 Yeah
 No, I I I do too
 I’ll be interested to see the comments to hear the comments uh as we always as we always do
 Robert, thank you
 Yes
 And don’t forget don’t forget to go to the website secondact
tv
 Look at our new merch page and and pick up Robert’s book, The Guys Guys Guy to Love and check the show notes for Guys Guys Radio and TV now all over the world with UK Health Radio
 Robert, thank you for your time as always and we’ll see you again soon on Second Act TV
 Thank you, Silka