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How Do I Date Someone? | Ep 06

What does dating look like after the first marriage? How can you make sure you go in with your eyes wide open and set yourself up for healthy relationships? In this podcast we'll talk about diving back in to the dating scene, as well as danger signs to be aware of.



    • Should you date again? Is casual dating right for you?
    • Danger signs to look out for when casually dating
    • Compatibility when looking for something more serious
    • Signs of a toxic relationship


It’s important to consider and clarify your goals when deciding whether or not you should date again.

What are your goals right now? Are you eager to get back in the social scene? Are you looking to have fun? Perhaps you’re interested in experiences outside of traditional monogamy? Or, you may feel strongly that you’re ready to explore a potentially serious relationship with the right partner.

However you envision your next relationship(s) unfolding, it’s important that you clearly communicate your expectations with your partner(s) early on to be sure that your intentions align.

Not only should you be honest with your partner about your expectations for dating, but you should be up front with yourself about how dating might impact your personal life.  It can be easy to idealize dating, but also consider the possible stressors and conflicts it may cause.


      • The claimed cupid. The claimed cupid is already in a committed relationship, and is hiding his or her relationship with you from their primary partner. Typically these relationships can be a ticking time bomb. 
      • Mr./Ms. Mystery. A mysterious suitor may be charming, but be wary of what’s beneath the guise.
      • The all fun and games guy/gal. Relationships should be fun, but pay attention to how you and your partner derive pleasure and entertainment. If your interactions are based largely around alcohol or drugs, this could be problematic, especially if either of you have a family history of substance abuse.
      • The honey can you…Be wary of anybody asking a lot from you, especially requests that make you uncomfortable or put you in physical, emotional, or financial jeopardy. 


“Opposites can attract because people can learn to find the middle ground; they can appreciate their differences, and they can teach each other things.”

You’ve heard that “opposites attract,” but also that “birds of a feather flock together.” So which is it? In healthy relationships, there’s a mixture of both. It’s nice to be in a relationship with someone who shares similar values, but isn’t your clone. If your partner stimulates and challenges you and exposes you to other interests, hobbies, and opinions, that can keep things interesting and spicy.


“It’s so important to be in a relationship where you feel safe–that you’re with somebody who’s trustworthy–whether you’re dating casually or you’re really looking for a serious, committed relationship.”

Some people are so smitten within the first few dates that they ignore red flags. I’ve worked with clients who have been charmed by their partner’s initial charisma and compliments, only to find themselves constantly criticized as the relationship progressed.

Toxic relationships are marked by patterns of you seeking approval from your partner after feeling insecure. Instead of constantly questioning yourself and your worth, it’s important to question instead if this person is right for you.



Podcast Transcription

[SUSAN]: After the First Marriage is part of the Practice of the Practice Network, a network of podcasts seeking to help you market and grow your business and yourself. To hear other podcasts like Empowered and Unapologetic, Beta Male Revolution, or Bomb Mom podcast, go to Welcome to the After the First Marriage podcast. I’m your host Susan Orenstein. We know that divorce is a painful process, whether you were the one that ended the marriage, or you were the one that was left in the marriage, or perhaps it was a mutual decision to end the first marriage, we know that there’s a lot of pain involved. Many people describe divorce as a grieving process, taking you from despair, sadness, anger and confusion, to a rebirth with new challenges, new opportunities, awkwardness, insecurities, and excitement and joy. You’ll see on my website that our logo is a rainbow – a sign of hope after the storm. In the After the First Marriage podcast, we’re going to sort through all the things that went wrong in your first marriage and your current struggles, in order to help you have a transformation, a brighter future over the rainbow. Please visit our website and you can sign up for our free ecourse where you’ll get information and advice about topics such as self-care, dating again, coping skills and co-parenting. Thank you for joining us. Hi, everybody, it’s Susan Orenstein here with After the First Marriage and I’m really excited today about our topic that I’ll be talking about with you, and that is about dating, dating 101. What does dating look like after the first marriage? And how can you make sure you go in with your eyes wide open so that you set yourself up for really healthy relationships? So, the first thing that I talk to my clients about, that I think is really helpful, is when they’re starting to talk about, “Well, should I date again? I’m interested in this guy,” or, “This woman’s kind of flirting with me, not sure whether to move forward.” The first thing that I suggest people look at is, what’s your goal? What’s your goal in dating? And when you can get clarity to that, when you can answer that question, you’ll be in better shape to move forward. So for some people, after their first marriage, they want to get back out into the social scene and have some fun. And it’s a cliche but they want to play the field and if that’s clearly what they want to do, then I say go at it and have fun, just know what you’re getting yourself into. So, if it’s casual fun that you’re looking for, to have a good time, maybe, you know, some people enjoy recreational sex, they don’t want strings attached, they don’t want to get serious, they just want to get back into having a social life, get back into the dating scene, getting in touch with feeling single again. Then just make sure that you are putting yourself in the situations and in your, you’re putting yourself in situations and with people that have similar goals and so that nobody gets hurt. So find a partner that’s looking for what you’re looking for and keep it casual. Find somebody who’s also fun loving and not into drama. And you may be saying, “Susan, I’m not looking to find someone I want to date a lot of people.” Well, that’s fine too. And I’m not even assuming that the people listening are wanting monogamy. So there are lots of people lots of, I’m a sex therapist too and I know that there are lots of flavors of sex and sexual variety and sexual activity people like. Some people want to have open relationships, some people like to swing, some people are into even like the BDSM world, and some people really are interested in finding a solo romantic serious partner. So, there’s not one flavor, there’s a lot of variety. And I encourage people to know what they want and to be able to express that but, while they’re on that journey, to make sure that they’re really clear with the partner or partners they’re with of what they’re wanting so that there’s honesty and integrity in the process and there aren’t any casualties along the way. So, maybe you’re not sure if a more casual type of dating and sex scene is for you. Maybe with your first marriage, you had a different style, maybe you were much younger and you’re not sure what’s possible for you and, and you want to be open to exploration. So, here are some things to think about to decide whether casual dating and casual sexual relationships are something that would be good for you or not. Think about the pros and cons and you might,you know, late at night when you’re by your bed, you could even come up with a list of some pros and cons about having casual relationships. And be honest with yourself. So one thing to think about is, what are the benefits for you of taking some time and dating and exploring? What’s in it for you? What could be some advantages? And then on the con side, think about what are some disadvantages and from what you know about yourself personally, are you somebody that tends to get very attached when you’re in a romantic relationship or in a sexual relationship and you are easily jealous or easily threatened? If that’s the case, then dating a lot of people and being with somebody who also wants to date a lot of people may feel very threatening to you and may just be a setup for failure. Be honest with yourself and be honest with your partner. And if you decide that you do want to go this route of dating many people, experimenting, experiencing different people, and enjoying that, think about still protecting yourself and being on the lookout for some danger signs. And what do I mean by danger signs? Well, this may go without saying, but it may not. Be on the lookout when you’re dating, for somebody who’s already in a committed relationship, maybe they’re married, maybe they’re partnered with somebody. If they’re lying, if they’re hiding that relationship from the other person, then there’s going to be a lot of drama. So, I’ve seen some people in the past to think that that’s a really safe relationship to be in when they’re getting to know themselves this, “Oh, I’m with this person, this married woman, this married man, they’re not going to leave their husband or wife so we can just have fun.” It may seem like that at the beginning, but what you have to think about is that that person is somebody who keeps secrets and is capable of being dishonest. And if they’re capable of being that way with another person, then they’re definitely capable of being that way with you. So you have to wonder, what are they not telling you? And you also have to think about what that’s doing to that third party that you don’t really know. So it’s very easy to distance yourself from a stranger like the married partner of somebody else and to not even recognize them as a person but they are a person. And believe me, and when I’ve seen people who have been cheated on in relationships, it’s extremely painful. And so really be honest with yourself about that. Do you really want to be part of that kind of duplicity and harm to another person? Now, some people are in relationships and they’re wanting to date and have a casual relationship and yet the person seems like a mystery person. And sometimes that could be a sign that they are hiding something, they are already married or they have some secrets. So, just keep your eyes and ears open to that, and denial can make things easy at the time but can lead to complications later. So if somebody has some mystery about them that might seem charming at first, you have to think there may be something underneath the surface that is not pretty. Other danger signs is when you’re dating and there’s a lot of substance abuse going on. So, I know some people drink and use some recreational drugs and they are able to handle it, it doesn’t lead to lots of problems for them. For many people, that’s not the case, that drinking and using recreational drugs becomes very problematic. And if you were dating someone in that situation, or if you find that really the source of having fun is going out and partying with that other person, just be aware and make sure that doesn’t take on a life of its own. Some people are able to enjoy that for a long time and other people have more addiction in their chemistry, so to speak. So, we know that there are some genetic markers that make some people more vulnerable to substance abuse patterns. So, if you know that that’s part of your family history, or maybe that you’ve already had some problems in your past with addictive tendencies, then be really careful when you’re dating to make sure that partying isn’t the main source of how you’re dating, because it’s really easy to fall into those patterns and it’s much harder to get out. One of the reasons I think it’s helpful to get this advice, I’m giving this advice to people now, is because it is so much easier to get out of a problem soon, so much harder to get out of a problem later. So, you think about it as, I think about it as quicksand that if you see that you’re in quicksand, you want to, well, you want to avoid quicksand at all costs and the later, the longer you’re in quicksand, the more disastrous it is. And so you want help right away, and you want to recognize you’re in it right away but what I want for the listeners is just that you can recognize quicksand and do not get in it. And so, some of the things I’m talking about, like dating someone with lots of drama, or somebody who’s married, or somebody who has a lot of secrets, can lead to a lot of problems getting out. And, you know, to my audience here, you all are already people who have been in situations that have not been to your advantage, and so that’s why you’re divorced, even even if it was your choice or it wasn’t your choice. So, I want to help people make sure that they learn from the past and then they learn from other people who have made mistakes, so that they can find some really healthy, loving relationships for their future. The other warning signs of dating and when you’re when you’re just starting to get to know people is to be wary of anybody that is asking a lot from you, that’s asking you to do things that make you feel uncomfortable, asking you to violate your boundaries, or asking you for things that make you uncomfortable about boundaries. So, for instance, if somebody is asking to borrow money or asking you to go in on a business deal, and maybe even without a contract and putting yourself, you’d be putting yourself in some kind of financial jeopardy, that is definitely a warning sign. Also, beware of anybody who’s asking you to lie for them, or to hide things for them. If they’re asking you to keep the relationship secret, these are all things to really take into account. So, I want you to have a lot of fun in the dating world, as long as, well not as long as, but please keep yourself safe. And please be aware of ways that people can emotionally manipulate you. So, if you’re somebody who’s looking for something serious and you know yourself enough to know that you don’t really want to play the field, you don’t want to have any kind of casual sex or be involved in casual dating. That’s fine and it’s great that you know that about yourself. So make sure that when you’re looking to date that you find somebody who has the same kind of values and the same desires that you have. So, how do you know who that person would be when you date? Well, there’s some common advice out there, like opposites attract. And then there’s the opposite advice, which is birds of a feather flock together. So, you may wonder, well how do I find somebody who’s really opposite me and that means we’re compatible or oh we’re too much alike and that means we’re incompatible? It can go either way and actually, in healthy relationships, there’s probably a mix, a mixture of both of those things. It’s nice when couples have similar values. So, I think the bottom line is that you have to have similarity in terms of your values, to have a foundation of integrity and trust, but it’s also really nice not to be in a relationship with your clone, to have somebody that stimulates you and challenges you and exposes you to things, their interests, their hobbies, their thoughts and opinions that are different than yours and that keeps things interesting and spicy. So, some extroverts are attracted to introverts, some couch potatoes are attracted to sensation seekers, some big spenders are attracted to those who are thrifty. In those ways, opposites can attract because people can learn to find the middle ground and they can appreciate their differences and they can teach each other things. So ,that’s what I mean by it’s a little bit of both, that you want somebody who’s different but also, in those differences, you find things that you respect and things that can inspire you. I wanted to talk about other danger signs, too, as we talk about dating today. It’s very common when you’re dating to find people that aren’t what they seem, that, you know, you can’t judge a book by its cover. So, we used to, in the good old days, go into a Barnes and Noble and look through books and really get to see what held our interest before we bought them. And that was fun. And so when you’re dating, somebody could look very appealing and attractive and then after you date them a few times, and you learn about them, you become disillusioned or you’re not quite enchanted, they’re not what they seem to be. I want to tell you that’s totally normal and, good for you, that you are keeping your eyes open, and you’re able to say that person’s not really a good fit for me. What I’ve seen in my practice is that some people are so smitten with people during the first few dates, that when they start to see things that they don’t want to see, they kind of close their eyes and refuse to see those things, and then the relationship keeps going and going way too long. I can give you an example… This example is from several of my clients stories kind of mixed together so I’m not really identifying any one person but, I’ve seen several women in particular who described dating a very charming, charismatic type of male who compliments them, and makes them feel really special. And then, after a few months, starts to find fault with them, and makes them feel really insecure. And in these patterns, I’ve seen the women go above and beyond to try to get the man’s approval. And then the man will give his approval now and then and the woman has become more and more dedicated to getting this man’s approval, who can be critical but also complimentary. And I’ve seen this enough to see that this is a dangerous pattern, that that person’s conditional approval and conditional love, it becomes very toxic. And so, and that can also happen with same sex partners, and it can also happen with women who can be very disapproving in heterosexual relationships. So, it can come in any shape or form. I wanted to highlight this situation to let you know that if you find that your partner is very judgmental and gives approval and gives disapproval, and you start becoming more insecure over time, that is definitely a dangerous sign. That’s a sign of a toxic relationship. And instead of trying to constantly improve yourself, I would hope that you start to question, “Is this person right for me? This doesn’t seem right. I’m with this person and I’m starting to question myself more and more.” So, that’s definitely a dangerous sign. In this podcast, we are going to be talking about different types of personalities, different types of personality styles, and how you know if you’re with somebody who is a narcissist. So, I was talking about the approval and disapproval pattern… There are other patterns that you may see when you’re dating. And in particular, a toxic pattern I see is when people are dating others with narcissistic tendencies. I am going to dedicate a whole episode on that because I’ve heard so many situations where people can get really charmed and then entrapped into these relationships and if the continuum at its worst, at its worst, I can see that people get into relationships where they are emotionally and even physically abused. And so that is definitely something that exists, it’s more common than people like to believe, and I want people to take their safety seriously and recognize that it’s so important to be in a relationship where you feel safe, and that you’re with somebody who’s trustworthy. That is key, whether you’re dating casually or you’re really looking for a serious committed relationship. So, to take your needs for safety seriously, that’s number one and the relationship can’t go far at all if you don’t have your basic needs met. I hope you enjoyed today’s After the First Marriage podcast on dating. We’ll have a lot of fun having guests talk about their experiences and see what light they can shed on these situations. And to sign up for our After the First Marriage course, you can go to to get our free course that has information about how to build your self esteem, self care, dating, navigating co-parenting, all kinds of things that divorced adults have to encounter and navigate in this world. Thank you for joining us. Thank you for joining today in After the First Marriage. For more information and resources related to loving yourself and your life after the first marriage, please visit our website This podcast is designed to provide accurate and authoritative information in regards to the subject matter covered. It is given with the understanding that neither the host, the publisher, or the guests are rendering legal, accounting, clinical, or any other professional information. If you want a professional you should find one.

About your host:

Susan Orenstein, Ph.D.

Dr. Susan Orenstein is a licensed psychologist and relationship expert  with over twenty years of experience. In 2005, she founded Orenstein Solutions, a private counseling practice in North Carolina that serves children, teens, adults and couples. 

She created the After the First Marriage Podcast to support individuals through the significant life transition of divorce. She whole-heartedly believes that “happily ever after” is an option for everyone, and is dedicated to helping divorcées regain the confidence to pursue a fulfilling future after the first marriage. 

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After The First Marriage is part of the Practice of the Practice Podcast Network, seeking to help you market & grow your business & yourself. To hear other podcasts, like Empowered & Unapologetic, Beta Male Revolution, or Bomb Mom Podcast, go to

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