“Hardballing” in Dating Over 50: Great Idea or Big Mistake? 5 Pros & Cons Explained

Five awkward dating situations that that you’re likely to encounter
 These are common
 Thank you so much for joining us again on Second Act TV
 Once again, I’m so happy to welcome back dating coach and relationship expert Lori Gerber
 Lori, thank you so much for being here again
 Great to be here
 our conversation today
 I found a blog, as you know, on your site, five awkward dating situations that that you’re likely to encounter
 These are common
 And I think it’s one of the reasons, too, why a lot of people are hesitant to go back out there
 They’re afraid of embarrassment
 There’s all kinds of dating fear
 So, I thought that this this might be a really good topic to address some of these likely awkward situations
 By the way, only I write my blogs based on what people bring me based on what happens in real life to my over 50 daters
 It totally got my attention
 I think that’s a it’s a great topic and I I want to ask you about one that wasn’t on here and then we’ll go to your five
 What’s super awkward is when somebody shows up and they don’t look like their profile pictures
 How do you handle that? It’s actually very common
 What I have learned is that the majority of people lie on their profiles about their age, their height, their body type, or they use outdated or in other some other way enhanced photos
 So that really is actually something that happens quite frequently and which is why I require my clients to have a video chat before they meet in person
 So that is where you can really see how close are they to their pictures
 You still can’t be sure, right? It’s there still could be a surprise in person cuz you don’t really know what the rest of my body looks like
 I could be who knows, right? But it gives you a much better sense of age, amount of hair
 But if you have skipped the video chat, then you still should have a half an hour date
 And again, I only think the the first date should be a drink, a coffee, a tea, a smoothie, right? It’s only a 30-minute date anyway
 You should have the date and see if you still could find yourself attracted to the person
 I think the the takeaway for me because this this would be so awkward and it would be difficult for me to say, you know, well, you don’t look anything like and people do do that
 You can get ve there’s some very rude be I mean it’s bad if you just totally misrepresent yourself
 I’m suggesting you have a half an hour date
 You have a half an hour to be kind to another human that ostensibly you’ve had a fun banter with
 So I don’t recommend conf confrontation
 I don’t recommend accusation
 I recommend getting to know a human and then after half an hour if you’re loving it stay
 If you’re not loving it and it’s not a match with a lovely you don’t think this is a romantic match
 I wish you the best of luck
 Yeah
 This is one that you hear over and over and over again
 So maybe just expect it, you know, just expect it and certainly don’t be surprised
 Yeah
 Don’t be surprised
 Exactly
 Exactly
 Well, let’s go over these five situations
 The first one here, he asks you to pay or split the bill
 And I say he because the other ones really pertain to both, but this is probably more for, you know, an awkward situation for a woman
 That’s that’s really tricky because again my hope is that you’ve bantered, you’ve had a video chat, you’re getting to know each other
 If money is sort of a trigger issue for you or something you’re grappling with or you’re scared about, generally this isn’t a problem, right? Generally, we’re waiting for the man to ask the woman out
 Generally, the man is paying for the first date
 After that, then it gets interesting
 But generally, that’s not an issue
 But if he says, “Will you pay?” or “Do you want to split it?” or “Do you mind if we split it?” or anything like that, then you just have to ask yourself, what are your values because you really might not mind
 You might not mind paying
 You might not mind splitting it
 You may be of that philosophy
 The only thing I think is is off is if someone asks you out and then asks you to pay
 That’s a red flag
 That’s weird
 That’s not a values or philosophy thing
 That’s just that’s awkward
 That’s truly awkward
 And in those cases, again, rare, you can say, “That’s weird
 I was expecting you to pay since you asked me and then listen to what he says, right? Like I’d be dying of curiosity to know what he says after that
 Well, I left my wallet at home
 Yeah
 Especially at our age, this is this is one that I just shake my head over be and maybe because we were just raised
 Yeah
 And the the man pays for the dates
 And I don’t say that because I I can afford to pay for it, but I I make up for it in different ways
 For me, there’s just something about when you’re in a restaurant and then the man pay
 So, it’s oldfashioned
 I get it
 But if I was asked to pay or or split the bill, that would be an immediate, okay, okay, sure, sure, I don’t mind
 I’ll I’ll do it
 There’s no second date
 99
9% of women expect you to ask for the date, plan the date, and pay for the date
 It’s it’s it is still very much a cultural norm
 Here’s here’s another good one
 They won’t stop talking
 Just talk and talk and talk and talk
 This happens all the time, too
 How how do you handle a a talker? Well, first of all, I like to keep drinking to a minimum, especially at the beginning
 For most people, drinking makes them more
 I actually met my husband when he was drinking and I didn’t realize he was drinking and I thought he was a talkative guy
 Boy, was I wrong
 Okay, so coffee, tea, smoothie for the first date in daylight, not at night, will get you more a sober personality is more the person’s actual personality
 So, that’s number one
 You might have a narcissist who really is totally self-absorbed, right? Like that’s that’s a possibility
 And then the third possibility, which is probably the most frequent, is that the person’s nervous, nervous, and they talk cuz they’re nervous
 Men really do think if they tell you lots of stories and they tell you all their credentials and they tell you how big the fish was, like they they do think they’re impressing you, right? So, you really do have to go, can I tell you a story? Or, you know, would you be interested in hearing my about my upbringing? or you know, you really do have to help them remember the balance because they are trying to impress you
 So for men, if you’re listening, try to make it 50/50
 For women, if you’re listening and the man’s talking too much, first of all, listen intently
 Make sure they think you’re actually listening because if they don’t think you’re listening, they’ll really go on
 You know, say back some things you heard and then segue that into, hey, I want to make sure make sure I tell you about blah blah
 Or you can even start a date like, hey, let’s take turns
 I get to ask a question, you answer, then I’ll answer, then you get to ask a question, and then that’ll be fun, right? That could also make them relax
 Well, and the big thing to remember here is, and we’ve actually done videos on it, is the most interesting people are the ones who don’t talk at all
 Well, not not talk at all, but the more you listen, the more interesting you become to somebody else
 And that that’s just a a fact
 If you just remember that if you do get nervous, although you don’t want to be too silent either
 It’s so funny
 My husband my husband’s actual personality is very very quiet and then but I noticed then that when he does speak everyone’s like what’s he gonna say you’re right okay number three here another situation that they reveal a health or money issue right up front and this is everyone’s biggest fear right everyone’s the biggest fear dating over 50 is like is this person gonna rob my purse or make me a nurse rob my purse or make me a nurse? Yeah
 Or or are they gold diggers? Yeah
 Are they going to take my Either way, right? Like literally all genders have this concern is how is this person going to impact my wallet and my time, right? My time and my energy
 Everyone wants someone healthy and wealthy
 And yet many of us are not healthy and wealthy and we’re not getting any healthier and wealthier over time
 So, it’s a tricky thing
 And the context you can hear me suggesting is, you know, most of us are not wealthy and all of us are going to have health issues if we’re lucky before we die, right? Like if we’re going to live old enough, we’re going to have some health issues
 So there’s nobody who is perfect and there are certain financial situations and health situations that will be okay with you, acceptable to you even f like I mean the reason my husband has arthritis and concussions is cuz he’s a jock
 Well, that’s also what makes him sexy and strong
 So, you know, you can’t have you can’t have everything, right? So, there are some health conditions that are going to be acceptable all the way to attractive to you
 So, you can’t be just you don’t want to avoid dating because you’re afraid of it
 And I’ve heard a lot of people do that
 I’m afraid if I date someone over 60 or whatever, I’m going to have to be their nurse or their purse
 I’m going to have to take care of them financially or I’m going to have to take care of them or I already took care of someone who died or who left you
 We’re scarred
 We’re really scared
 So again, there’s a lot of obstacles to believing in love and going for it
 Some of them quite deep
 But in that moment where one is revealed, again, this is good
 You want it revealed in the first few dates
 And the next thing you should do is, how does that affect your life? How has that affected your relationships? How has that been for your partners? Just start to ask a question and care and be a good friend because the worst that can happen is you are a nice person they met
 The best that can happen is it was the love of their life
 But there is no reason to react, get angry, be judgmental, be rude
 If someone’s being vulnerable enough to tell you their financial or their health issue, be kind
 Yeah
 Listen
 Be kind
 Be generous
 Ask questions
 And then if at the end you’re like, I can’t personally handle that thing
 That’s not in alignment with my dreams, then you need to have your canned response
 Remember, I give all my clients the canned responses
 It’s been lovely to meet you
 I think there’s a a mismatch here because I promised myself I would not date a recovered alcoholic again
 I promised myself I would never, you know, date someone who couldn’t match my financial desires for travel
 I promised myself I c I would not become a caretaker early in a relationship because I just got done caretaking my disabled kid
 But it’s from the heart
 It’s kind and it’s and you have to be honest with yourself
 But wait till the end of the day
 You never know
 There are people who fall in love with people who are dying
 There are people who fall in love with people who are poor
 It happens every day
 It’s not it’s not a dealbreaker because it’s a dealbreaker
 As you said, at our age group, that’s going to happen more and more
 People wonder about it and some will will reveal it or as in point four here, uh what if you’re asked, you know, maybe it’s not revealed, but somebody says, “So, what you know, how how many medic or how much medication do you have? What’s in your medicine cabinet?” Um, honestly, if you’re working with me, I say you bring it up in on the second or third date because it’s more like, “What are your health issues?” Not, “Do you have any?” Right? I remember I I’ll never get over my client who was like, “My sexual health is impeccable
 How’s yours?” And he said, “Very good
” Which meant, I only have herpes
 It’s just like you can’t you have to actually ask the exact question you want to know, right? Like if you and and even then people may lie to you but at least you asked
 So I actually think you should ask before you’re asked and then based on however vulnerable they are with you then you decide how vulnerable you want to be with them at that stage in the relationship
 Um if you’re asked and you haven’t gotten to ask for it first I say you tell the truth because it’s going to make sure it breaks you up sooner if the person is not a match
 You want somebody who can accept your issue, is charmed by your issue, or can tolerate your issue or work with your issue
 If it breaks you up, that was not your person
 And you need to again prepare
 This is one of the things I do with all my clients
 Prepare your spiel
 Prepare how you’re going to say it
 You know, the first time I ever had sex in 1971, I didn’t know about herpes and I didn’t use a condiment
 Thank god I didn’t get pregnant, but I did get herpes
 I’ve been treated for it and whatever it is
 Okay? or you know I was uh treated for cervical cancer five years ago
 I’ve been clean
 I go for for yearly checks but there’s no my doctors feel absolutely confident that I’m great but because of it I eat a very low sugar diet and I avoid alcohol
 You know it could be not a financial or health thing but whatever that is you have to be ready to talk about it in a succinct self assured confident way
 And it really works
 I’ve seen this work for my clients over and over again
 Well, and like you said earlier, it’s not about, you know, do you have issues? What are it? Is what are they? What I struggle with and and you’re absolutely right in all of your recommendations
 I still struggle with, you know, it’s it’s too early
 It’s none of your business
 I mean, it is if you’re going to go forward, I I I struggle with this one on a first date
 Maybe, you know, it doesn’t have to be the first date
 For me, it needs to be before you have sex and by the fourth date
 Because the problem with not doing it is once you get to the fourth date and beyond, you start to get attached
 And if you’re attracted to the person and there’s enough good on paper, you then start to build real and then if you have sex, especially, you’re now really starting to build a bond and fall for someone and you want to keep them, but maybe their health issue or your health issue is a deal breakaker
 And I don’t think that’s fair to have somebody agree to something not knowing what’s inside
 Yeah
 You have to really decide, can I live with Yes
 It’s a tough one
 and and it’s something and if you don’t trust them enough to say it, they might not be your person
 Sometimes, you know, you can deal with more once once you do get to know somebody better
 But is that a good idea? Number five here, then finally, he pushes for sex too soon
 And I say again, he because this is usually the man doing it, not not the woman that they probably wouldn’t complain
 You never know, but you never know
 But I will it is obviously a gendered thing and you know to the men listening I would say you know make them beg much less wait and you tell them you’re withholding sex that makes a woman very horny
 That really is the case again where you don’t want to shame someone
 You don’t want to be judgmental rude
 You might fall in love with this guy
 You really might as long as he responds well to your, you know, could we slow this down? And that’s the right response, you know
 Oh, I’m very flattered
 I’m glad you’re attracted to me
 I’m attracted to you, too
 I really like to take things slower
 I’m not that kind of girl
 Like I, you know, I would want to be monogous before, you know, engaging in sexual activity
 Um, and I certainly don’t think we’re ready to have that conversation yet
 So, you know, let’s stick to public places
 I’m happy to make out in the alley with you, but that’s about as far as far as it’s going to go right now
 Or your version of that, right? That’s just a an example
 But it’s a very nice, very sweet, especially if you are, if you’re not attracted, then it’s like, you know, no, no, thank you
 And it’s been lovely to meet you
 You seem like a wonderful person
 I don’t think this is a romantic match
 I wish you the best of luck
 But if you are attracted and you do like the person, you just need to slow it down
 Then then really being upfront about what your requirements are to move in that direction is really a healthy thing
 And then how he responds could turn you on more
 Another big conversation that would go under this, we won’t go to in detail here, but the sex on the first date is that everybody has an opinion about that and and yeah, we’re old enough to we can do whatever we want, but what are the the the you know, what’s the consequences of that? It’s something you’re you’re likely to run into
 So, be yeah, so be prepared in how you want to handle it
 And it doesn’t mean sex does not mean the same thing to any two people
 and it certainly tends to mean something different for women and for men
 So, we should all be aware of that when we’re proposing it or declining it
 There are risks and rewards to that choice
 And if you’re looking for your long-term companion, I certainly suggest you do not have sex on the first date because it will cloud your judgment
 Yeah
 Be prepared for how for how to handle it
 Well, those are the five that you have in your blog
 Is there anything you want to add before we before we shut this down? you I want to give a context which is that the awkward conversations are not to be avoided they’re actually necessary and you want to lean into them you want to reward them if they come up because that’s what’s going to have you realize if you’re really compatible with somebody all the all the pleasantries and all the fun conversations and all the oh my god me too and I love Aspen too and blah blah blah like all of that is great for building the chemistry and the rapport but what will really determine if you’re compatible what I call liability compatible, not just asset compatible, is when those awkward things come up and you weather that
 You both show that you can tell the truth, be vulnerable, be connected, and also just whether or not your answers are compatible
 That’s where the actual strength building of the relationship happens
 So, we don’t actually want to avoid it
 Good, good advice
 Well, if you have any moments to share that we didn’t cover here
 I I think I really think these are some of the big ones, but I would love to hear our viewer
 What kind of experience of awkward moments? Exactly
 Get those comments coming
 Lori, thank you
 I always just love talking with you
 It’s always always a fun time
 If you want to have more fun with Lori or just get her advice, all of her contact information is below
 She’s a great great coach
 You have great information just on your site
 So, your your website stuff is there, too
 Thank you so much, and I look forward to our next conversation on Second Act TV