Dating over 50: What’s the 3 Date Rule? Essential Dos and Don’ts for First Second and Third Date!

Being in this business for so long, what I have learned is the major pitfall is that we get tired. We get tired and we get jaded from dating. So I'm doing everything I can to help my clients not get tired and jaded. Thank you so much for tuning in again to 2nd Act TV. So happy to welcome back Lori Gerber, dating coach, relationships expert, and you were or still are a resident expert on a lot of the dating sides, which gives you even more of a unique perspective on a lot of stuff that we're going to talk about today. So Lori, thank you for joining us again. My pleasure. I was, I am not currently. And what it does give me is a breadth of experience with tens of thousands of daters. So Lori, on our last segment, we discussed what is your type? Do you actually know what you're looking for when you are dating? Very interesting segment. I will link to it. So you have some of the basics here that will apply to our discussion today, which is first date tips and mistakes, as well as the second and third date. If I'm quoting you directly here, the first three dates are the most important dates. They're kind of the only important dates in my opinion, in terms of determining your type, right? Determining whether or not you're with your type. So our last segment was all about figuring out for yourself what your type is. This segment is really about figuring out is this person your type? Well, let's talk about specifically then what quote you should or shouldn't do the do's and don'ts of first, second, and third dates. Let's start here right at the beginning that whether you're doing the asking, meaning our men or women for that matter, that's a whole other segment, or you're being asked on a date that dinner is unnecessary, that that's one of the big mistakes. Being in this business for so long, what I have learned is the major pitfall is that we get tired. We get tired and we get jaded from dating. So I'm doing everything I can to help my clients not get tired and jaded. I don't want you stuck in a two or three hour dinner. Now, and sometimes I will say there are some exceptions where somebody is chivalrous, you know, especially we're talking about people over 50. They still have some more what I would consider old fashioned ideas about dating and they really want to take you to dinner and maybe they're lonely and maybe they want a night out even if you're not the person. You don't have to say that yes to that. It's not a deal breaker if you say yes to a dinner, but I only want you going on dates with someone you have chemistry and rapport with. So first of all, you need to have a video chat first to see if there's chemistry and if you're attracted and if they're real. And second, when you go on that date, I recommend smoothie, coffee, tea. And then if you're really into it, you can take a walk and then you can have dinner. So I'm not against a traditional first date. I am against a traditional first date of dinner if you are not attracted, if you are not having good synergy. Yeah. And that's really good advice for our guys too, because still, especially in our age group, they're still the one doing the paying or they feel awkward if they don't. And then that can add up fast. So, you know, why? Yeah. Yeah. Why? Why do that? And you're, as you said, you're stuck. You're stuck. If one of you wants out, it's difficult to leave a dinner. Right. It's like the old joke of, you know, call me at seven and say there's an emergency. Not necessary if you're having a coffee and you only need 20 minutes to see is the banter good? Am I attracted? Could I, could I imagine kissing this person, right? You don't need two hours, two hours. And people are planning two hour dinner dates because they're lonely, not because they know you're the person for them. Well, my, my first date with my boyfriend, we now went together 13 years. Yeah. It was going to be a drink and then we talked for four hours. So it can happen. Short can turn long, but long is very hard to turn short. Exactly. And then number two here, the second mistake, a lack, and this is really something to think about, a lack of preparation. You know, do we ever really think about preparing for a date other than what we're going to wear and how our makeup is going to look? So much on that. So much on hoo-ha, not enough on head and heart. Exactly. And it's, and, and what, what people have trouble with the most, most, most people, I think that's a generalization that's accurate is, is what to talk about. Right. A lot of debate about this. I would go back to the first segment you and I did together to review. There are three voters in all of us that the head is voting on. Is this practical? Does this look good on paper? The heart is voting on how does it feel? And the hoo-ha or the heat is, am I attracted? Does this turn me on? The good news is. The hoo-ha is kind of becomes self-evident. I'm hoping in a video chat and certainly in an in-person date, you don't have to ask, you know, you don't have to ask a lot, right? You can kind of see it. You can feel it. You have to ask yourself, do I want to kiss this person? Am I attracted? But for the heart and the head, you need to have pre-designed your questions and people really are not good at this. I cannot believe that people still go into a date asking yes or no questions. You know, do you want to retire soon? Do you like hiking? Do you know, beach or mountains, right? Like questions that do not elicit interesting answers. And I give a boilerplate list, you know, you can have a boilerplate list. No, you had some really interesting ones that I want to talk about, give something specific to our viewers. Like you had, like, how do you spend most weekdays? That's really important, especially at our age, if we're retired or halfway there, that can tell you a lot. And it's so much better than saying, what did you do for a living? Or what do you do for a living? Or what do you do? It's the language is actually so much more inviting to somebody. Because again, men are thinking women are trying to find out how much money do I have? And how's my prostate? And women are thinking he's trying to find out how fast can I have sex? And you know, will you take care of me? Right? Like everyone's got the stereotypes that the other one that we think we're asking the questions for. So if you can ask questions that don't put someone on the defensive or feel like they have a right answer. That's cool. Right? What's an ideal Sunday for you? How do you spend your weekday? What's your favorite thing about your siblings? That's fascinating. What do your friends go to you for? You don't go, do you have friends? And that's what they want to know. They want to know, do you have friends? But you don't say that. You don't say that. That's rude. I think, you know, there's two questions that I think everybody wants answered when you first start. I mean, I think they're going to come up and we need to either think about how we're going to answer them or, you know, how to avoid them. And that is how long have you been divorced or about your status? How long have you been single? Maybe if you've never been married or divorced. But what they really want to know is why are you single? And they really want to know, are you really available? That's what they really want to know. And there are better ways to find that out and ask that. How long have you been divorced? Doesn't tell you anything. That's a number. What did you learn from your marriage? What was the divorce like for you? Those are questions that are not only going to give you more of the answers you want, but it's going to make the person think and show up as themselves in a way they can't even avoid it because you're asking them a question they didn't pre-think of. You have to have your answers prepared too. And let me tell you, if you don't, you're not even going to want to go on dates. I was coaching some friends of mine in the car over this past weekend, and each of them had to create, I call it a spiel, each of them needed a spiel on herpes, divorce, why I've never been married, right? Like those are things you need a quick, honest, upbeat spiel about. And if you don't have one yet, it's either because you're not ready to date yet, which is fine, or you haven't thought about it and practice on a friend. But you need that for dating, not just because the other person wants to know and they need to know, but to boost your confidence. And what that will tell you, again, in my opinion, if you prepare yourself with these questions, and as you just said, ask yourself how you would answer that. You'll also know whether you should ask that in the first place, which is something I learned when I read through some of your questions is, I wouldn't want to be asked this. Oh, tell me the ones you didn't want to be asked. Well, like, okay, if you could change one thing about yourself, what would that be? That would annoy me, where somebody else might really- That's a third date question. That's a good third date. Because remember, if you like someone and that person's going to work for your life, then you really actually want to fast forward getting to know them. Especially since I don't recommend having sex until you really do get to know them, because then the sex will be better. It then behooves you to really actually talk about what doesn't work about you, not just what you love about yourself, because that's going to come out anyway, eventually. Right, exactly. No, it's interesting. Like I said, I'm not putting a right or wrong on it. It's interesting what that could evoke in someone. So if it's something that's uncomfortable for you, it may not be uncomfortable for the other person. But if you can't answer it either, then I would suggest- Well, then definitely don't ask it if you don't want to answer it. Exactly, exactly, exactly. Well, then of course, one big reminder in whatever you talk about is to stay away from any negativity, right? Right. So again, the problem we have is that we don't actually resolve our past baggage, and we bring it with us in heavy suitcases to our current date. And then our date can tell something's wrong, or something's off, or something doesn't feel good. But they don't know why, because they didn't do anything. So we want to keep our past in the past, which doesn't mean they're not going to eventually find out all our stories. They are. Those are not secrets. But if you come in with negativity, they're going to know you're not resolved, and you're not truly emotionally available. So I'm not saying hide it. I'm saying actually do the work to get resolved. You know, from interviewing so many different people on this show, Laurie, and relationship experts, dating coaches, you know, therapists, whatever, there seems to be a diverse opinion on talking about your ex on the first date, or asking about it. I think that if you are divorced, again, this is my opinion, everybody does want to know. Right. But what do you recommend? Do you stay away from it? So I prefer what have you learned in your past relationships, because then if they're ready to talk about their divorce, they can. And if they're not, they won't. If you do not have the rapport or the attraction, it does not need to come up on the first date. It does need to come up by the third date, right? Like it does. It does. Because by the third date, you're deciding if you really, if you can make something of this, but you don't have to say, why did you get divorced? Well, let's move on to the second date. What are the three mistakes? So the first one you say, don't agree to or and or don't ask to go someplace that's loud. You don't go to theater, don't go to a movie, etc, where you really can't talk. You really need to get to know the person. And people hate me for saying this, but also don't drink. And nobody agrees. And if you're going to drink, drink one drink and, you know, keep your hand on it. It just isn't conducive to the purpose. The time for you to to consume entertainment together is the eighth date, the tenth date. In the first three dates, you should be obsessed with learning about one another and how you would get along. Well, and that leads into, you know, don't kiss or more, don't have sex on the second date, which a lot of people do. And it never really leads to a serious. Well, I shouldn't say it never does, but it more often than not, it does not get too serious. Yes. Exactly. Men and women have different reasons for having sex early. There could be the reason that you just want to have sex. If you just want to have sex, either hire it or be very clear up front, not have sex with somebody who is looking for their long term person and who really wants to get to know you. Conversely, a lot of women will have sex to, well, number one, because they're drunk and they just aren't actually making good judgment. They feel flattered or they will do it to try to increase the heart age for him. That doesn't work. It's a bad bet. It's a bad bet. The man's trying to increase the increase the rating for her. She's trying to increase the heart rating for him. Again, it's a bad idea. No one ever regrets waiting, especially what I don't want you to do is kiss. If you're not intending to take the relationship further, which people do, especially when they're drinking, because if somebody offers it, how are you going to say no? It's a recoverable mistake, but it wastes your time. It makes you fatigued. It makes you trust yourself less. It gives you bad ideas about what dating is. So my rule for my daters is no kissing unless you're going to have another date, unless you like the person. No kissing. Yeah. What's funny about our discussion is that it sounds like we're in high school and it doesn't and it doesn't change, especially if that's the last time you dated was back in high school or college. You're right back there. It's true. We haven't grown up. But what do you mean by don't leave with any mystery? That was point three. So again, remember, I'm all about less fatigue, less disappointment. So what I can't stand is, and I'm sorry, it is usually women, but men too. Either the man will go, do you want to go out again? And she'll go, I'll get back to you. Or he won't say anything at the end of the date. She won't say anything at the end of the day. And it's like, was it good? Did we have a good time? Are we going out again? And the amount of time, and then you're all weird on the sites because you're like, am I seeing this happening again? Just the amount of exhaustion and drama is resolvable with the following rule. And that is you don't leave the date without saying how you think it went. If you're the woman, you say, I had a really good time. If you asked me out again, I'd say yes. Boom. Now you're going to find out. You've showed your cards. He now has to show his cards. If you're the man, I had a really good time. Would you like to go out again? And you will know by the answer, right? If it's not, yes. Or if it's not, how about Thursday? That's probably a no. Assume it's a no. If it becomes a yes in a text the next day, fabulous, but don't go home wondering. Don't go home. Yeah. That is so important. So important. How you leave people wandering and it can be really cruel. You know, I really believe dating has a lot of karma to it and you want to treat other people the way you would like to be treated. Exactly. Well, let's move on to the third date. Now the third date is like, that's the ultimate date. According to you, I agree with you that when you got to the third date, there's interest there and you need to get to some serious stuff. And the first one you say is, or the mistake would be avoiding the deal breaker questions, avoiding talking about, well, what really matters to you. And this is really hard because people don't, the first and second date, if you're getting a first date and a second date after a video chat is because you're attracted, you want to hook up, your head is happy with how they look. And if you got a second date, you're getting along, you feel good. And if you're in a third date, all of that should be going very well. And so the idea of now bringing up, I have herpes, or I have a kid at home still, or I have to take care of my sick mother. I can't leave the state. I actually don't have any retirement savings, or I'm out of the country half the year. My estimate is that most people have about seven of those things. I call it liabilities, right? Between health issues, lifestyle issues, I'm allergic to cats, bad personality traits, bad habits, and vices. Nobody doesn't have them. So if you're on a third date and you're not hearing about the liabilities and not talking about yours, you don't know. And I do not recommend going on a fourth date and falling for somebody whose liabilities you don't know. Because the person who is right for you is a person that has seven liabilities that are either adorable to you, acceptable to you, or you can work with them. If you're not talking about the liabilities, you're not bringing it up, you're investing in crypto. You can think, or like this came to my head, so I'm sure it did with others, is that, well, aren't some of these, you know, do you really have to do with that early? Is it, you know, do you maybe do get to know each other a little bit more and then talk about this? But the thing is, if it's something that is going to eventually come up, it'll be an issue when it comes up if it's going to be an issue now. I think it's truly disrespectful to decide when to tell someone if they're falling in love with you. I mean, you know how you feel when you find out later someone lied or told information. It doesn't feel good. It almost invalidates all the time you've spent together pretending you do know the truth. And again, when the person is the right match, and I know this from many, from my personal experience and many other people's, when the person is a match, they're going to be like, what's the next one? What's the, okay, I can handle it. Oh, how are we going to handle your mother? How are we going to handle your kid? How are we going to handle your prostate? How are we going to, because they're in love. That's good. It's a great point and so important to think about. The last two that, well, we've talked about this a lot already, but having sex before commitment. By the third date, you might have long-term potential. People don't like this either, right? People don't like that I only give three dates to figure out if the person is eight or above in all three ages. People don't like that I say don't drink. This is dating like you mean it. If you just want to waste time and get tired, do it your way. This is not moral. This is just about saving time and disappointment and heartbreak. They also don't like when I say literally don't have sex until you're monogamous, right? That's different than saying don't have sex till the fourth date. I'm saying you have three dates to decide, would you like to try monogamy with this person? You have three dates to find out if they're interested in monogamy or not. Obviously if you are and they're not, that's a deal breaker, abort the mission. But if you both want to try monogamy, that's when you would say you don't need to be monogamous with me now. We just got to know each other, but I wait to have sex till I'm monogamous. It's important to me, right? It's a big step for me and I want to have a certain level of intimacy before, during, and after. Yeah, and it's a sign of a long-term relationship that there's long-term relationship potential because maybe you'd be monogamous with somebody you want to be with but not necessarily with somebody you wouldn't. Well, you're showing your hand and then you'll see their hand. And if they run away, it's because they thought three dates would be enough to get laid and they were wrong. Or they might go, well, let's be monogamous because I'm dying to have sex with you. Well, finally, oh boy, my goodness, time goes by fast talking with you. Continuing if you aren't into it, that that is a big mistake. If you really, you know that it's not going to work or something really bothering you, but you still go out, you still keep going. It is the biggest mistake we make because we do not want to be alone. And that desire to not be alone translates into picking wrong and then staying, which is just so dangerous to your fatigue and your heart. You're not looking for the same things. If your dreams and goals don't intersect, you got to call it by date three, even though it means we're going to go back to date one again with someone new. Well, Laurie, what a, yeah, this was what a spunky discussion. I learned a lot as usual. I love these discussions. I hope our viewers did as well. If you want to get a touch with Laurie directly, all the, all her contact information is in the show notes below. You can coach with Laurie, especially if you, you know, some of these things here, you want to know a little bit more about, and I will link to our first conversation because that really gives a good, a good basis to what, what we just discussed. So Laurie, thank you so much for your time. I really, really appreciate you coming on Second Act and I look forward to our next discussion on Second Act TV.