5 Tough First Date Questions You Need to Be Ready For

questions that you need to be prepared for when you’re out there dating. And most of us want to say, none of your damn business. [laughter] [music] Thank you so much for joining us again on Second Act TV. Once again, I’m so happy to welcome back Sandy Weiner, the dating coach, relationship expert, the founder of Last First Date. Sandy, thank you so much for being here again. Thank you for having me again. Well, today I want to talk about something that I I know you deal with all the time. You know, the questions that you need to be prepared for when you’re out there dating. And there’s five, well, very common, very common questions. And and these questions are not just common. They can be tough if you think about it. And they’re certainly certainly annoying. Yeah. And the more you prepare, the less you’re just going to be annoyed and you’re going to actually be able to answer these. You’re also likely to ask them. So, you might want to think twice before asking them or asking them differently. So, this I I think we’re covering a lot in this segment. So, let’s let’s get to the first one. The first really common, tough, annoying question. Why did your marriage end? Why do we always say it like that? But yeah, why did your marriage end? And most of us want to say none of your damn business. [laughter] Um, but there’s a question beneath the question. And most people don’t want to know about your whole marriage. They don’t want to know how your marriage imploded, exploded. They’re asking other questions. And these are the ones that you should be prepared for. What they’re really asking is, can you take responsibility for your part in why the relationship ended? Have you done some healing? Are you actually emotionally available to me? What’s in it for me? [laughter] I mean, that’s really why people ask these questions. And the you mention it or you alluded to it. When you’re talking about your ex, one of the one of the uh wrong ways to answer this is to blame everything. you know, oh well, my ex was crazy and just re maybe he was, maybe she was, but that is just that’s that’s almost a a end the day question now because so many people talk about this. Well, it’s a red flag on you actually because you paint yourself as a victim and a person who points fingers and blames. Maybe they were crazy, maybe it was a really hard marriage, but the point is keep it short. You can say something really simple because this is just a new person that you’re just getting to know. They don’t deserve the whole story. You can say something like, “We both really wanted it to work and unfortunately we grew apart. It ended and we’re amicable or we’re not amicable.” Like whatever. It doesn’t matter. That’s that’s all you really need to say is we wanted it to work. It didn’t work. I’m looking forward to meeting the right person now. you know, and I learned a lot in that relationship. And we’re not saying that the other person, you know, shouldn’t know about your marriage or why it ended, but that’s not the first date. That’s just a question you want to get through and and because it it can really go wrong. The next one, this one, I don’t get, but yes, you get it all the time. So, why are you still single? Well, I I’m single. I mean I mean, why does somebody who’s single ask somebody else why are they still why are they still single? What am I missing here? You can be really cheeky and say, “Well, I tried being double, but it didn’t work [laughter] out really well.” They’re really asking, “Are you too picky? Is there something wrong with you?” Right? Are you available to me? Am I going to regret dating you? So, you want to reassure somebody that maybe you’re discerning, you know, that you’ve dated a bunch of people, you’ve had relationships, you just haven’t met your forever person yet, and you’re really looking forward to it. But what a lot of people do is they will say, “Well, dating sucks. The apps suck. There are no good people. All the good ones are taken. Everybody’s either, you know, married or gay or whatever.” You know, like people say things and again it paints you in a bad light. Yeah. And we have a whole episode actually on that. It’s a good question, but not for a first date. So here number three here. And I I know I always hated getting this because like where where do you start your answer? What are you looking for? So you know what is it that you want? What are you looking for? Yeah. So you can say I’m looking for GDAU. I’m waiting for GDAU. No. [laughter] Um no. But what they’re really asking for is are we compatible? Are we looking for the same kind of thing? Are we both looking for commitment? Are we looking for casual relationships, marriage, companionship? All of these things that are important in the long run and hopefully if you’re dating online, a lot of this should be in your profile. These are not things we really need to ask each other if people are being honest. You do want to answer honestly without saying too much. This is not a job interview. You’re just going to say the bare minimum. So, I’m looking for a long-term relationship with somebody who’s kind and compassionate and really wants a relationship. You know, is going to prioritize relationships right now. Just keep it fairly vague because it’s a first date. But you do want to know if a person is just dating casually and it’s not looking they’re looking for a hookup. I mean, people do usually will say that on a first date. You know, I’m really not looking for anything right now. I’m not ready for a relationship. I’m just out of something. Good. Thank you. Um maybe I’m out of something five minutes ago, too, and I want to just date casually. That’s fine as long as you both have eyes wide open and you know what you’re looking for. But but don’t go into too long of an answer and be honest. you know, we’re we’re we’re addressing these questions with the understanding that at least you have the intent [laughter] to be honest and thus don’t say this or don’t say that and why why were you know we bringing that up but this yeah this one is can be very misleading so I don’t know like I said I how accurate of an answer are you actually going to get or you know are they people pleasing women especially do that and I say that because I did I Not, you know, not out of any bad intent, but I when I like someone and and they said something that, you know, you know, I do this. Oh my gosh, you know, that sounds so exciting. [laughter] That’d be fun. And I meant it when I said it, but but but no, I didn’t. That’s not me. And that’s got me in trouble a couple of times. Being too agreeable or Yeah, that sounds amazing. or the opposite where you just don’t really know what you’re looking for and you’re too vague and then but somebody’s going to say, “Well, I don’t really want to date you because you don’t you don’t really know what you want.” Okay, question number four. And again, you are so likely to get this and it can be very annoying depending on uh you know how you feel about it. When was your last relationship? you know, basically when ho how long have you been single? Well, that’s what they’re really asking is is but some people will get like a deer in the headlights with that one because they don’t really want to say I’ve been single for 10 years, you know? So, what they really want to know is, are you available again? Did you just end a relationship last month? Am I your first date after your divorce? Am I your rebound? It happens. And it doesn’t necessarily mean anything. What’s more important is are you open? Are you ready? If you really want a relationship and they want a relationship, are you on the same page? So, don’t go into a lot of detail. They’re going to judge you for whatever you say. This is what we do on first dates. We judge each other. We’re taking words out of context. We’re making up stories because somebody shared something. So, share as little as possible. Be as concise as possible. be as positive as possible. Tell them what you’re looking forward to. You know, I have been in some short-term relationships since then, and I’m really looking forward to finding my forever partner. How about you? What are you looking forward to? Would you say interesting to see what you think about this? Would you say it is somewhat of a red flag if not the red flag, maybe yellow flag or something to think about if somebody says they’re just newly out of a relationship? Doesn’t that warrant some other considerations? I think you have to know more about the circumstance. So, there are lots of relationships with people I’ve worked with that somebody was separated for a long time. For whatever reason, they didn’t end the marriage. They still lived in the same house. Maybe they lived on separate floors. Maybe they moved out, but the relationship hadn’t quite ended yet for insurance purposes and they kept them on their insurance. We don’t know. We don’t know if they’re going to go back to an ex, if they’re not going to go back to an ex. Get curious if you like this person. Find out what the circumstance is cuz everybody has a different story. Well, the the reason I asked it or it popped in my head again because that actually happened to me. I really like this one guy, but I was his first his first date. I mean, we ended up have like a three months relationship, but then he ended it or he said he, you know, he just started dating and he feels weird getting, you know, this this serious already. I mean, I’m I’m glad he did because that would have been a disaster, you know, and and and I’ve heard other people say, “Well, if you’re online dating and they just starting, you know, don’t get too attached.” So, I I I don’t know. I I don’t know if that is or isn’t, but some, you know, again, something to think about. I think you’re right. You have to have more information, but you also can’t predict. You can’t predict anything. Like, you can listen to the way they talk about their relationship. Listen to whether they say they’ve been through therapy or have done some healing. I didn’t date for two years after my divorce. And so, I was separated, living in the same house for three years. and then two more years. So, it was a long time. But when I started dating, I was not ready to commit to the first person for sure. I wanted to explore. I wanted to have fun. And I told people, I’m not ready to commit yet, but I am dating seriously to eventually commit. That’s my goal. So, be as honest as you can be. All right. The last one here, question five. I don’t you might not get it quite in this verbiage, but what what does your life look like? You know, what what does your what does your day look like? Interesting question, but what are they really asking there? Do you have time for me? [laughter] Do you have time for a relationship? I mean, we often talk about our busyiness. I have children and they are the most important thing to me. Like, people write this in their profile. It’s the stupidest thing to write in my opinion. I mean, I hope you you don’t hate your children or they don’t hate you. I hope that they’re important to you if you have them, but if you’re looking for a relationship, you want that person to know that they’re going to be a priority. So, you’ve got to be able to convey that. So if you’re expressing your whole life story as, oh, I spend, you know, this amount of time, I spend three months with this kid and three months with that kid and I go to pickle ball on Mondays and then I have my this class and this class and I travel and I, you know, it’s like, oh, so you’re trying to time slot me in here, you know, on Mondays at three. That’s what it can feel like. And sometimes, if you’re like me, when I started dating, I wanted people to think I was busier than I was because I thought it was cool. Yes, I’m starting a new business and I’m so cool and I’m busy all the time. And people really got the impression that I had no time. So, be careful how you express that you have time or you don’t have time to date. That’s all they really want to know. You know, it’s like I I’m looking forward to having a partner. I have so many passions. I’d love to share them with a partner. I love to travel. I’d love to do that with a partner. It would be so much better with a partner. I love to cook. It’d be so much fun with a partner. You know, really good point. You know what does a day have activities that you could easily bring somebody into? Uh that that again with my friend who I mentioned before, he was a widowerower and for a few years and he played literally played golf every day. He kept himself busy like that. But then when when they got together, you know, she now plays with him during I mean he he absolutely made room because the room was there for a relationship. He kept busy because he wanted to be busy. That I guess that could be the reason as well. Yeah. Sometimes we’re busy because we don’t have a relationship. But if we’re rigid, we don’t make time. If we’re not rigid, we learn new skills. We learn how to play golf. You know, we the person who’s playing golf all the time doesn’t play golf anymore. I mean that’s that is an important thing and I think another question a way to ask this would be if if you had a day that was unplanned without work what would you do how would you fill that day and that way you can find out like how what a person loves to do how they would fill their time you’ll find out their values what they prioritize I think that’s important information more than what does your life look like right now because people may not tell you the truth Well, we’re starting to get to towards the end here, Sandy. There there was one other question I thought was interesting and I wonder what you think about it. Is what should someone dating you know about you? I thought that’s so interesting, but is that a good question to ask? Well, they’re asking if you have any flaws and what have you what have you screwed up in the last relationship? I personally wouldn’t ask somebody, do you have any red flags? Like, are there any flaws that we need to know about you? I don’t think people are honest enough. I mean, people are wanting to know. Are you aware of yourself? Are you going to be honest about yourself? Do you know yourself? Well, most people are not going to say, you know, I have a tendency to shut down in arguments. It’s not going to happen. If you do want to ask that question, I you probably want to say something about yourself to if if you want that kind of honesty, that kind of introspection, maybe say something like for example, one thing you should know about me isah. But uh it’s a it’s an interesting way to to dig a little deeper and see what somebody, you know, will say. It might be kind of fun to experiment on a first date. [laughter] Yeah. I mean, people can answer it in a way like, oh, some a flaw that I have is I’m just too nice. [laughter] I just care too much. I do. And I’ve gotten my heart broken. I I’m the first person who shows up with chicken soup when people are sick. H gez. I wish I could change. Oh, that’s funny. I’ I I’ve actually heard stuff like that. [laughter] Anyway, the whole point again of this conversation is that if you are going to be new to dating, you’re going out there, these are questions really to expect because you want the answers as well on some on some level. So, it you have to think about it. You have to come a little bit prepared. Sandy, what what do you want to leave for our viewers on this? I am such a big advocate for preparing answers to questions in general and dating because you know these are going to be asked. So come with your fabulous answers. People ask you what do you do for a living? Come with a good answer to that. I mean you are the PR representative of your life. You get to decide how to talk about all these things. So, if somebody’s going to ask it, and they will, prepare your answers, and then when you get to know them better, you can go deeper, but not on a first date. They don’t deserve your full story yet, and it’s too much. It’s too much too soon. Well, if you would like a little help answering these questions, it’s really, it really is a good exercise. Do give Sandy a call. a lot of I know that you’re you’re working with several of our our viewers and I get some really good feedback. All of Sandy’s contact information is below as well as a link to her podcast, Last First Date Radio, where she covers a lot of this as well. You’re always just full of wisdom, Sandy. I always say that. [laughter] Thank you, SA. As always, I really, really appreciate your time and I look forward to our next conversation on Second Act TV. [music]