Five Questions To Consider When Dating A New Guy


Have you ever been afraid that the next guy is going to turn out just like the last guy? If so, I’m going to give you a five-step process to evaluate if he’s worth your time BEFORE you get in too deep. You’re gonna want a pen for this one.

Have you ever doubted your own judgment when it comes to picking the right man? If you’re single, chances are the answer to that question is yes. So what questions should you ask yourself during that first month of dating? Stick around to find out. 

Hi, I’m Evan Marc Katz, Online Dating Coach for Smart, Strong, Successful Women, and your personal trainer for Love. Welcome to the Love U Podcast. Stay to the end of this video to discover the five questions you should consider when dating a new guy. When we’re done, I’ll let you know how you could apply to Love U to create a passionate relationship that makes you feel safe, heard, and understood. 

Today, I’m going to talk about five questions to consider when dating a new guy. When people come to me, it’s because they’re not trusting their own judgment because of a track record that hasn’t been a particularly successful track record. Everybody is looking for a shortcut to make sure they don’t make any mistakes and get hurt again. And so I tried to distill the kind of questions I want you to ask yourself, regardless of whether you’re in Love U coaching with me. These are questions you could ask yourself when you’re dating someone in that first month to know if you’re on the right track and continue investing your time in a guy. So the first question, again, I know it sounds stupid, but I’m gonna I’m going to list five different things. 

Number one is, do I like him? You would be amazed. Maybe you wouldn’t be by the number of women that work with me, who contact me on the phone or on Zoom and tell me they don’t like the guy that they’re seeing. What should they do? I don’t know if I want to go out with him again. I just would rather be home watching Netflix. I just don’t feel up to it. I got to like talk myself into going on this date and something just feels off about this guy. We don’t really click. So why are you going? I don’t know. Because, you know, you say you should open up to different guys now. That’s not what I say. That’s not what opening up means, going out with someone you don’t want. So, let’s just establish this. If you don’t like a guy, don’t go out with him. Spare him the trouble. Spare yourself the trouble. You’re not doing anybody any favors by going on dates where you’d rather not be there. I was number one. Do I like the guy? 

Number two, how does he treat me when we’re together? And that’s sometimes misleading, right? It’s important. Why would you go on a date where you feel mistreated? Why would you go on a date when you’re not with a guy who is thoughtful, considerate, sensitive, a good listener, chivalrous? With the qualities, we want to see in men. How does he treat me? Does he make plans in advance? Does he live up to his word? Is he flaky or inconsistent? Do we want to pay attention to how he treats me when we’re together? Is it always his way or the highway? Is he making plans or is he considering my needs? Is he making sure I’m having fun? So how does he treat me? The problem is a lot of bad guys know how to game that system, bad. I don’t like the word bad, but a lot of guys know how to game that system. A guy who’s good at dating, who is charismatic, could show you a great time when you’re together and you can say, well, I like him. He treats me well when we’re together. That’s like a false positive. So that’s sort of the dividing line in this little video is most of my clients know the answers to one and two. I like him. I like being with him, but haven’t thought through the next three questions. So anyone of these questions is a disqualifier. What’s the point of having their relationship or having a story play out? We already know that it’s not going anywhere. Because A. You don’t really like him that much. B. He doesn’t treat you that well when you’re together. So most women get seduced by the first two. I like him. He treats me well. 

Third question, how does he follow up when we’re apart? Did a video on this recently. It’s worth repeating. Good ideas are worth repeating. It doesn’t matter if he took you out to a fancy dinner, looked in your eyes, told you that he loved you, took you home and made sweet, sweet love to you, and made you breakfast the next day. All that matters is how quickly he says after that. That was amazing. When can I see you again? Text four days later, it doesn’t matter. The men are making plans in the indeterminate future. A week later. Two weeks later. Oh, I got a really busy week. Let me follow up with you then. Let me check my schedule. It doesn’t matter. It is useless, so I really want to pay attention to number three. How does he follow up when we’re apart? Again, it’s very easy to be seduced by a guy who you have chemistry with, who treats you well, comes on really strong, trumps the literal pants off of you, and then he doesn’t follow through quickly. Now, it doesn’t mean that every guy’s going to be enamored with you and want to commit to you after a great first date. Most guys worth their salt have options and are not going to be that blinded. Generally, we want to see your relationship start to ramp up. We’ll talk about that in another video. 

Question number four, are we good together in the short term? And what that means is sometimes you’re at a time in your life where you want different things. You can say that we’re really great. We’re having fun. But if his life is in turmoil right now, then you’re not really good in the short term. You might be good on paper. You might be good in the sack. But where you’re at in your relationship, because he’s separated, because he’s going through a messy divorce, because he is on shaky ground with his job, because he’s going through a full midlife crisis and there’s a lot of layoffs going on right now. There’s a lot of reasons that a guy might not be a good short term fit. And so we have to pay attention to those reasons, not sweep them under the rug. You could really like a gun. He could treat you well. He could follow up quickly. But if his life is a mess and he’s not in the position to give you what you want. Don’t sweep that under the rug. Pay attention. Are we good together in the short term? Can he make me happy? Is he showing the ability to do so not just because I like him or I’m attracted to him or he’s a nice person, but does he have anything to give? 

Are we good together in the long term?

Question number five, are we good together in the long term? And again, I know that’s the $64,000 dollar question. Are we good together in the long term? If I could answer that question for you, I would be a very, very successful man. The Nostradamus of dating. But there are signs about whether you’re good together in the long term. These are signs that we can pick up on in that first month of dating. Let’s dig into those feelings. I got a story about a client who was dating a guy for one month who was madly in love. As a client, 10 years madly in love with this guy. And my coaching changes when someone’s in a relationship, then when she’s single. Single, I’m trying to get her into a relationship. Now she’s got a boyfriend so we’re really talking about the relationship and the guy and what she observed one month into the relationship before she graduated from coaching with me. Was that her boyfriend was arrogant and dismissive. She still had a great time with him. He told her he loved her. He was financially generous. It was a whirlwind of a ride. But when she tried to speak up, expressed her opinion, he was kind of dismissive of her. One year later, I checked in with her and sometimes I check in with some of my favorite clients. I checked in with her. And sure enough, she’d recently broken up with her boyfriend for the very reason that she spotted in the first month that they were together. He was completely dismissive of her and her opinions, and he made her feel small, unimportant, and unseen. So are we good together in the long term and can take on different metrics, right? Compatibility is not whether you like the same stuff or have the same background or the same religious belief. That’s not what compatibility is. I have a whole week of content in Love U about compatibility. And it hinges on things like introversion and extroversion and a relationship to money and a libido and a desire for sex and how we view family, how we handle household help. Household chores are neat together. How we communicate and resolve conflicts. There’s  a whole bunch of things. Not in the least of which do we want the same things in life. Do we want kids? Do we want to get married on the same timeframe? You don’t have to ask all these things point-blank, but you need to keep an eye on them lest you find yourself in love with someone who is on a different train, different track than you are only to find out one year later. Oh yeah. That guy told me at the beginning he wasn’t looking for anything serious and I ignored it. You got that. So those are the five questions. Gonna run down one more time. Do I like him? How does he treat me when we’re together? How does he follow up when we’re apart? Are we good together in the short term? Are we good together in the long term? And sometimes in the first five to six weeks of dating a guy before you sleep with him, before he becomes your boyfriend, you need to feel really good about the answers to these questions to take the next step, to avoid making mistakes, to avoid wasting time, to avoid getting hurt. I’d rather you cycle through a new guy every month and ask these questions and get it right than to dive into a new relationship, only to discover six months later, you didn’t ask the right questions at the beginning. Got it. 

My name is Evan Marc Katz. 

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