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.

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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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Join our conversation (13 Comments).
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  1. 1

    Evan, you are just the best. Thanks for another thoughtful, informative video. I’ve looked a lot of dating coach’s websites and think you do the BEST job. You are both personable AND you provide great advice. Thanks, I appreciate you so much.

    1. 1.1
      Evan Marc Katz

      My pleasure, Jan. I truly love my work and appreciate the time you took to offer kind words.

  2. 2

    Another good article that made me think. Here is the list…

    1. Do I like him?
    2. How does he treat me when we’re together?
    3. How does he follow up when we’re apart?
    4. Are we good together in the short term?
    5. Are we good together in the long term?

    If I really like someone, I sometimes get stuck on #3 and #5. For #3, I MAY make excuses for him, or accept his excuses (like being really busy at work). For #5, I MAY just ignore red flags because I am optimistic that we have other things that make us compatible or there are other things about him that I like that prompt me to ignore the red flag.

    I only end up wasting time, because I eventually – usually more quickly now that I have in the past – I come to realize that this person is just not a long-term match for me.

    Here is an example of #4and #5 in action. I went out with a man a handful of times. I liked him and had fun when we were together. Yet I noticed that he would refer to women as “that b*tch I work with” or my ex’s mother is “such a b*” and that “b* only got to where she was because she slept her way to the top.” The first time he said it, I figured he didn’t like his co-worker. But after hearing him say this about women about seven different times, I realized that he had issues with women and I would probably eventually be the b* in one of his stories.

    No thanks! Not a short-term or a long-term match for me! Glad I paid attention to the red flags and didn’t make excuses for him.

    1. 2.1


      Do you mind elaborating on what you mean when you say “how does he follow up when we’re apart?”

      1. 2.1.1

        Sure! Evan does a really good job of summarizing, but I can share my own examples from recent dates.

        I had a recent date with someone I will call “A”. We went out twice, and then I had plans to go out of town. Date 1 – A planned a nice dinner on a patio. Texted me to say he had a great time, then made plans for the following weekend. Date 2 – Also very fun. Texted to say he had a great time. While I was out of town, he texted to see how my trip was going, then called to make plans when I returned. That’s great follow up.

        I also had my third date with a guy I will call “P”. P and I just had our third date, which went really well. We went for a swim and had lunch and a cocktail. Very fun! He looked me in the eyes, told me how much fun he had, kissed me good bye, and told me he couldn’t wait to see me again. I got a text with the same message the next day. Then, a phone call a week later. That’s it. No plans for a fourth date. No more phone calls or texts. He let me know he’ll be busy with company taxes and a few other things.

        That’s the difference between good follow up, and not good follow up. A is interested and is available and he acts accordingly. P might be interested (or not), and he’s not that available and he acts accordingly.

        I could give 100 more examples, but it’s about feeling like the man is trying to move things forward. That’s why follow up is important. He makes a move, and I respond. And it keeps going like that. If the pieces and parts fall in place, then we might move into a relationship. If not, it flounders. Follow up is key.

        1. Bbq


          Do you ever txt first?

      2. 2.1.2

        BBQ – Early on, I try not to text first. It just feels better when the guy does the outreach. It sounds old-fashioned, but it’s one of the few ways I can gauge how interested / available he is.

        1. Bbq


          And he? How does know? Or feel?

        2. SparklingEmerald

          Hi Roz – Early on with my husband, sometimes I would try to send him an e-mail “first”, but whenever I would log on to send him and e-mail, there would already be one waiting for me. After awhile with so much back and forth e-mailing between dates, who went “first” became hard to discern. BBQ – As to your question “How does he know ? ” Well with my husband, he was very confident and just assumed I felt the same towards him as I did toward him. I remember reading one of his e-mails thinking “He seems a bit presumtuos, talking about “our relationship”, then I broke out in a big smile and thought to myself ” . . . and I like that. ” Of course, my actions on a date gave every indication that I really, really, liked him, and he was confident enough to pick up on that, but yeah, pretty much from our first date, he assumed that we were becoming a couple. 5 years later, here we are, happily married.

  3. 3

    Thanks so much Evan; jumping into dating after doing a dating detox for six months. Healed from the past mistakes, want to make sure I avoid wasting time, getting hurt, spending too much time with someone who is not a match hoping it will change when the signs are there that it will not. Thanks for keeping us on track. All the best to you Evan!! 😀

  4. 4
    Hairy Palms

    Roz, Roz, Roz…
    Not sure how old you are. I’ll be 52 in 2 weeks.

    I can’t speak for all men, but me? If it’s one thing I’ve observed in my past behavior towards women, it’s that yeah, I was the one pushing things forward. Towards sex AND marriage!

    Call it ‘the dance’ if you will, but darn it , I want something MUTUAL. Reciprocal efforts.

    You mention responding to his efforts.

    I can’t tell you how many times I’ve written messages and have women respond with answers but no questions.

    I think maybe your a naive expecting men to do all of the leg work.

    1. 4.1
      Emily, to

      “I can’t tell you how many times I’ve written messages and have women respond with answers but no questions.”
      I don’t think this has anything to do with you imitating contact. These women are just rude or self-involved. You are emailing them to open up a dialogue, a back and forth to get to know each other. If they can’t do that, that doesn’t bode well for future interactions. I’d just move on.

  5. 5

    This is brilliant advice EMK! It’s been years since I’ve dated and I also rarely dated in my teens and 20s. Now that I’m in my 30s and having to start over, I must say I barely know much about dating and reading your blogs and listening to your podcast is helping me get clarity and knowledge that I never possessed! Thank you so much!

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