If you found the previous article on relationship red flags for dating the divorced man helpful, here are seven more red flags that you should keep a look out for if you are trying to choose relationships that will have the greatest likelihood of success and happiness.
Raise your relationship red flag radar if:
He Expects You to Act as His Therapist
In a perfect world, by the time you enter into a relationship with a divorced man, he would have already done the work necessary to heal from his divorce and move on from his previous relationship.
But we all know that doesn’t always happen, unfortunately.
He might still be processing some residual feelings—they could be positive or negative feelings—about his divorce and previous relationship.
That can be normal and even healthy. We all have a past, we all have baggage, and talking about it with a friend or a loved one is one way to process the feelings and get through it.
What isn’t normal or healthy, however, is when those conversations start to become the only ones you’re having anymore, and you’re starting to feel like talking to him is getting to be a real downer.
If you find yourselves talking, night after night, about his feelings surrounding his divorce, and if you realize you are wiping his tears more often than you are laughing or having fun together, it could be a sign that he’s still very preoccupied with his previous relationship and not emotionally ready for a new relationship with you.
He Gets Angry and Defensive about Your Questions
On the flip side of him wanting you to be his therapist is the guy who doesn’t want to open up to you at all.
If you are both dating each other with the intention of having a long-term partnership, it’s not unreasonable to ask why his marriage fell apart.
I probably wouldn’t ask him that on a first date, but if you’ve been dating for some time and it looks like it’s getting serious, ask him in a way that feels comfortable to you.
It isn’t selfish, or rude, or prying for you to ask questions about his kids, family, life, and ultimately his divorce.
He had a life before you, and if you’re going to be part of his life right now and part of his future, it makes sense to want to know where he’s coming from.
If he seems opposed to answering your questions, think about why he’s not willing to go there with you. Why isn’t he willing to let you get to know him better?
The better you get to know someone, the better the chance you have of figuring out whether he’s a good match for you.
If he thinks that what matters to you shouldn’t matter, you have to wonder whether he truly cares about what’s important to you.
If he doesn’t want to go there with you, it’s likely that it will be very difficult for the relationship to grow in a way that really matters to you.
You Feel Guilty or He’s Trying to Make You Feel Guilty
Guilt can come in a lot of different forms. Guilt is that voice within that makes you second-guess yourself and ultimately feel really bad.
If someone is trying to manipulate you into feeling guilty, that tactic is really toxic to your relationship because your partner is not being real with you; they’re ultimately trying to control you and how you feel.
If you’re feeling guilty without anyone else trying to manipulate your feelings, it could be a sign that you’re not honoring your truth in some way; you’re not telling a truth that you want to tell or you’re not taking action on something that feels true to you.
For example, for some women, there is guilt that surrounds dating a man who is separated or in the process of divorcing. This can be a personal thing and determining where those boundaries are is completely up to you.
Or maybe you’re experiencing guilt around wanting to leave a relationship. If you’re feeling guilty for wanting to leave a relationship, check in with yourself on what concerns are coming up: What do you worry will happen if you leave? And are you taking on more responsibility for your partner’s wellbeing than is healthy?
Are you’re talking yourself into staying in a relationship that you don’t really want to stay in, because you don’t want to be another person to hurt or “abandon” this man?
If you find yourself having those thoughts, you’re taking on more responsibility for your partner’s feelings than is healthy. He’s a grown man. He can handle your leaving.
And if he says he can’t, then he doesn’t realize his own power to choose how he feels about a given situation; he’s putting all that responsibility on you, and that’s not fair—or healthy.
You Start to Resent Him or the Relationship
Unless his kids live on the other side of the world, they will likely be an everyday part of his life and his ex wife is someone he will have to talk to with some kind of frequency over the years to come.
Dating a divorced man means coming to terms with his baggage and how that might affect your relationship going forward.
But if you find yourself resenting him—for any reason: whether it’s his kids, his ex, his late hours at work, or even how much TV he watches—your anger and resentment could be pointing to a need or requirement that’s not being met in your relationship.
If resentment is coming up for you, check in with yourself to determine what exactly is making you unhappy. What do you want that you’re not currently getting in your relationship?
He Has Trouble Keeping It in His Pants
Cheating can be a complicated act and not every man who has cheated is necessarily a cheater by nature, nor will he always be a cheater.
But if the man you are now dating reveals that his divorce was caused by a series of infidelities on his part, or if you hear through others that he has a history of cheating, then it is fair to assume that he might also have some very real issues remaining faithful to you.
Unless he has recognized this as a problem and/or is seeking some professional help (coaching, counseling, therapy, etc) to get to the root of his inability to stay true to his partners, he hasn’t done the inner work, nor does he have the conscious awareness necessary to really change his behavior.
He Likes His Secrets
Similarly, it will be very difficult for a relationship to grow and flourish in a meaningful and fulfilling way if you can’t be real with each other, confide in each other, and have real emotional intimacy in addition to physical intimacy.
If your recently divorced (or even long divorced) beau is secretive and private about how he spends his time when you aren’t around, be concerned about why he isn’t forthcoming about these areas of his life.
If he doesn’t want to be open with you, and you get the sense that he’s not being open with you, it could be that he’s hiding something about his life that he doesn’t want you to know.
Whether he’s hiding some areas of his life out of shame, guilt, or sadness, it’s never your lot to heal him or make him come clean with whatever he’s holding back. It’s not within your power to force his issues into the light; he’s making a choice to not be forthcoming.
And you can likewise make a choice about whether being in a relationship with him would truly be fulfilling for you, based on the experience that you’ve already had with him.
Intimacy and relationship growth requires shared openness, trust, and a sense of safety.
If those qualities don’t exist in your current relationship, it will be difficult to achieve deep levels of intimacy.
It’s certainly possible that a man who has recently gone through a divorce may have a difficult time determining what he wants next.
After all, you’re probably reading this article because you yourself are trying to figure out whether or not this man is right for you.
In a divorce or separation, there can be so many mixed feelings surrounding the split and similarly, there is sometimes a lot of fear and uncertainty about entering a new relationship.
But if your relationship feels like a roller coaster and you’re on again, off again, on again, off again, or your guy has jerked you around—going back and forth between swearing he wants to be with you and then pushing you away when things get uncomfortable for him—try to remember what your intention was (your big “why”) for getting into a relationship with this man in the first place.
Are you dating him just for fun, or with the intention of finding a life-partner?
Clearly, he doesn’t know what he wants.
But if you’re clear on what kind of relationship you want, you don’t have to waste your time waiting for him to make up his mind.
Sometimes, however, women have a hard time moving on because they really like him, are very attached to being with him, and worry that if they move on, they’ll ”miss out” on being with him.
But let me offer a different perspective: what possibilities and opportunities for a happy, healthy relationship are you missing out on by waiting for this man to make up his mind?
Sometimes we stay stuck in relationships that drive us crazy because we won’t believe we can get any better. We believe in scarcity; that there are only so many fish in the sea, so you better “take what you can get”.
But if you believe that, then you’re probably not going to make yourself available to have a more fulfilling love life anyway, because you don’t believe you can get what you really want.
What do you need in order for you to get what you really want, in life and in your relationships?
When we really care about a man, or we desperately want for things to work, we sometimes ignore these red flags and ignore our gut feelings… We hope that by doing this, that everything will eventually work out.
Unfortunately, it rarely does.
Has there ever been a time when your intuition has been wrong?
When we choose to ignore red flags, we’re choosing to be unconscious in our relationships. We’re choosing to ignore the little whispers of truth and guidance that we hear when something rubs us the wrong way, even if we can’t articulate or even know what exactly it was that gave us pause.
We just know something wasn’t right.
If you’re sensing something’s not right, pay attention.
Something valuable is there… It’s nudging you closer to the life that you truly want and deserve.
Whatever the issues are in your relationship, if you find yourself agonizing over questions like…
Is this relationship worth it??
Should I give him a chance or walk away??
I totally get you. I felt the same way when I was dating, which is why I created a free guide to help you get clarity.
In my free guide you’ll discover:
- 30 questions to ask yourself to help you decide if you should give him a chance or if you’re wasting your time
- 22 red flags you should be aware of if you want to avoid heartbreak and painful surprises
- How to assess your compatibility with your partner to know if your relationship has long-term potential
Want to avoid wasting your precious time? I hear you! Download my free guide Should You Stay or Go? Relationship Choice Assessment ↴
Looking to get relationship help (beyond reading blog posts)? Here are a few ways that you can get real clarity and support:
- Trying to decide if you should give him a chance or walk away? My video course How to Clearly and Confidently Decide if You Should Stay or Go, is the best place to start.
- Dating a separated or recently divorced man and feeling stressed and confused trying to navigate the complexities of this relationship? Book a 1-on-1 Relationship Clarity Session with me.
- Want private relationship coaching and support to help you break free from anxious attachment so that you can ultimately have a healthy, loving committed relationship? Apply for a complimentary 75-minute Relationship Clarity Strategy Session to learn more about how we can work together to create the life and relationship you want. ❤️