11 Red Flags When Dating A Separated Man | Don’t Ignore These

Things to keep in mind before pursuing a relationship with a separated man

Dating experience | | , Editor-in-Chief
Updated On: February 5, 2025
red flags when dating a separated man
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It’s not easy to find yourself drawn to a man who is separated from his wife but not legally divorced. No matter how good being with him feels or how solid your connection seems, a part of you is always on the lookout for red flags when dating a separated man. This is exactly what happened to Julie, a midwife and birth doula, who met a separated man on a dating app and started seeing him. 

She recently wrote to Bonobology, seeking direction from our panel of experts on whether or not her decision of dating a separated man was right. “My partner has been separated from his wife for three years now but the divorce is not even close to coming through. We have been dating for 4 months and about two weeks back he asked me to be exclusive. He’s talking about us taking a week-long trip together and sometimes alludes to what it’d be like for us to live together. But never talks about the status of his divorce proceedings or when the divorce is likely to be finalized. 

“While I’m excited by the idea of being in a committed relationship with a man I’ve come to adore, I cannot help but worry about the fact that legally he is still married. Also, his being so closed off about his divorce makes me worry about whether this relationship has a future. I’m 38, and have no interest in being a perpetual girlfriend to someone or ending up in a dead-end relationship.” 

The fears and anxieties around dating a man going through divorce had me intrigued, and as I delved deeper into the matter, I discovered that there are many women like Julie, out there, wrestling with the dilemma of whether or not to date a man going through a divorce. So, I thought it apt to put together this detailed guide on dating a separated man, addressing questions about whether it’s ever okay, the green and red flags you need to be mindful of, and ways to navigate this complex relationship without letting it take a toll on your emotional well-being. If you’re currently on the fence about dating a man who is separated but not divorced, read on to get some clarity on how best to handle this situation.  

Is It Okay to Date a Separated Man?

The first question that comes to mind when you find yourself drawn to a man who’s separated but not divorced is, “Is it okay to date a separated man?” As this OP on r/AskWomenOver30 asks, “I’m starting to see a man that’s been separated for about a year but the divorce is stalled arguing over properties that he came into the marriage with. He has two kids and I have one. I’ve never dated a guy in this position and I’m very new to dating since having the baby myself. I’m honestly really really excited about him because he seems super into me and I’m super into him too. I’m 30 and he’s 36. What is the hard wisdom that I can maybe avoid learning the hard way?”

You see, dating a separated man is bound to bring up such concerns because it’s the grayest of gray areas when it comes to relationships. The man you’re dating or considering dating is technically single and technically married at the same time. While it has all the markers of a potentially complicated relationship, it’s not necessarily a bad idea. Whether or not dating a separated man is okay, ultimately, boils down to the specifics of his situation and what you’re comfortable with. To decide whether or not it’d be okay for you to pursue this connection, here are a few factors you need to consider: 

1. What’s his situation?

dating a separated man
Is he ready to invest in a relationship?

Whether a man dating while separated is a red flag depends on the specifics of his situation. For instance, if he has been separated from his wife for years and the divorce hasn’t come through because of the red tape or certain contentious issues they haven’t been able to hash out, he may have had the time to process the upheaval of emotions over his marriage falling apart and be in a place where he can turn over a new leaf. 

Being at peace with his past, not being aggressively hostile toward his ex, or still being hung up on her are some signs a separated man is ready to date. On the other hand, if he’s fresh out of a marriage, he might still be navigating grief, guilt, or anger. In that case, you need to ask yourself: Is he ready to give you the emotional energy a relationship requires?

Dr. Rachel Summers, a relationship counselor, advises, “Before committing, make sure you understand the nature of his separation. Is it amicable? Are there unresolved conflicts or legal battles? His emotional availability depends largely on how he’s handling this transition.”

Related Reading: 7 Important Things To Know About Dating While Separated

2. What are his intentions?

Before you end up falling in love with a man going through divorce, make sure you understand what his intentions are or what he seeks from jumping into the dating pool when his marriage is not even cold yet. Why is dating while separated? Is he seeking genuine companionship, or is he trying to distract himself from pain? Psychologist Dr. Mark McCarthy says, “Some people jump into dating too soon to fill a void or escape loneliness. Make sure he’s dating you for the right reasons—not looking for a rebound relationship.”

3. Are you ready to handle the complexity of this relationship?

Dating a separated man comes with baggage, more often than not. For example, he might still have financial or co-parenting ties with his ex that require them to meet and interact on a regular basis. Now, even if there is nothing going on or left between him and his ex, all that history can complicate things. Are you emotionally prepared to handle it? If not, dating this man may not be for you, not because you’re not right for each other but because the circumstances aren’t. 

4. What does your gut say?

dating while separated
Listen to your instincts

How does being with him make you feel? Do you feel secure? Or do lingering doubts and insecurities creep in? Are you able to believe his version of the story without any second thoughts? Or do you worry that there may be more there than meets the eye? Are you subconsciously looking for red flags when dating a separated man or do you feel at ease? These feelings, thoughts, or even physical sensations can be a manifestation of your instinct for self-preservation, and trusting them is essential.

Dr. Summers emphasizes, “Your comfort matters as much as his story. If something feels off, it’s okay to step back and reevaluate.” Dating a separated man isn’t a one-size-fits-all situation. If he’s genuinely ready for a relationship and you feel confident in his intentions, it could work out beautifully. But if his unresolved issues weigh you down, walking away from a separated man is a completely valid choice too.

Related Reading: 21 Huge First Date Red Flags You Should Be Wary Of

11 Red Flags When Dating A Separated Man

Dating a separated man can be an emotional rollercoaster. As this OP on r/Divorce, who has been dating a separated dad, learned when she was already too deep in the relationship. The man she’s with has been separated for four months, out of which they’ve been dating for two (at the time of her post), and eventually, anxieties and insecurities began to creep in.   

She says, “…He talks about his ex a lot… which had me concerned a bit at first…. but I get it, every experience he’s had since a teenager she was there, so it’s hard… For context, she ended things with him. He then tried to get her back, went to therapy and everything. She refused to do the couples counseling and said they were done. Then he started online dating as a way to cope… Then she goes and says she wants him back…and he says NOPE he’s done! Then he met me…. and said things changed. 

“Since his ex has realized he’s definitely seeing someone… she’s messaged him novels…about how she’s never going to give up on him and how she thinks she can get him back no matter what. The other day, he and I were talking about what we think “cheating is”. I said emotional cheating like flirting with exes while with someone and asked him if they happened to flirt at all lately, he got all nervous and then showed me his phone, it was novels upon novels of them texting lots…hers were emotional and his were a bit also but he was in no way flirting. 

red flags when dating a man with a child
Are you going to get sucked into his marital drama?

“…We are laying in bed in the morning. His ex called 5 times in a row, but he was on a phone call already so didn’t answer. Then she calls again, and he answers, she is at their old house moving HER things now, and she’s asking him about all sorts of pointless nonsense. Then later while eating breakfast she calls 2 more times again to waste his time while he’s with me. He lets her go eventually,  and then after an hour or so, she calls again and he doesn’t answer. Then texts her to say ” I’m busy”, and she replies “Call me later, I don’t care if ur busy with ur STUPID gf! ” I felt a bit upset about that, I told him he should stand up for me and that was a bit rude of her.  

“…He then gives me a heads up later that night that she asked him to do Xmas morning with her and the kids to which he agreed. He also told me a week ago she asked him to do co-parenting therapy together and he also agreed because it would benefit the kids. But now I can’t help but feel flooded with anxiety!! I’ve not felt this way about someone in so long, but I’m terrified about this situation at the same time…How can I make this work?”

As you can see, navigating the complex equation where your partner has an ex who isn’t technically their ex yet can lead to an emotionally draining relationship and can bring up fears and insecurities about the future. To make sure you don’t end up being consumed by someone else’s marital drama in the hopes of finding love, it’s absolutely crucial that you pay attention to these red flags when dating a separated man and reassess your decision to be with him if you spot any: 

Related Reading: 7 Myths About Men And Divorce – Busted

1. He’s not legally divorced yet

One of the biggest red flags when dating a separated man is the fact that he is still legally married, which means he hasn’t fully closed that chapter of his life. Dr. Summers states, “A man who is still legally married may not be emotionally or practically ready to commit to someone new. Divorce can be a long and draining process, and unresolved legal ties can complicate relationships.” 

Being “separated” is often a gray area. While some may use it to signify the end of a relationship, others may still be sorting out their feelings or hoping for reconciliation after the separation. Besides, divorce involves emotional and logistical disentanglement, which takes time. Without legal finality, there’s a risk he could backtrack or have unresolved ties with his ex. This is especially concerning if the man you’re with has started dating shortly after separating from this wife. In that case, there is a good chance that he is dating to numb the pain of his marriage not working out or using it as an unhealthy coping mechanism to deal with the separation.  

2. He speaks negatively about his ex

Dating a man going through divorce is not a good idea if he exhibits hostility or negativity toward his ex. Labeling her as the “crazy wife” or placing the entire burden of the divorce on her, saying things like she was controlling, she was a narcissist, or calling her names indicates emotional immaturity and a lot of unresolved feelings at play. 

Hearing him talk negatively about his wife may make you think that he’s over his ex but it couldn’t be farther from the truth. If he’s still venting anger, he may not have emotionally moved on and may still be emotionally tied to his ex through resentment. “If he constantly criticizes his ex, it might indicate unresolved anger or bitterness,” says psychologist Dr. Mark McCarthy, “This negativity can seep into your relationship.”

Related Reading: 15 Signs He Is Still In Love With Your Ex And Misses Her

3. He’s secretive about his separation

As we saw in Julie’s case, her partner’s reluctance to open up about the divorce and separation became a source of anxiety and insecurity. That’s what lack of transparency in a relationship does. It’s definitely a red flag because it indicates that the man you’re dating may have something to hide about the knitty-gritty of his separation. If he avoids discussing his separation or is vague about details, it may mean he’s hiding unresolved issues or is unsure about moving forward with you. 

“Secrecy about the separation’s timeline or reasons suggests he might be hiding something, such as lingering ties to his marriage or unresolved conflicts.”

—Ava Torres, relationship coach 

4. He rushes into the relationship

While it may feel flattering when someone makes you the center of their world and showers you with attention, rushing into a relationship can be a coping mechanism to avoid dealing with the pain of separation. Dr. Summers warns, “If he’s pushing for commitment too soon, it could be a sign he’s using the relationship to distract himself from the pain of his separation.” That’s because a healthy relationship requires time to develop. 

If your partner is glossing over that process and is taking things forward at a pace that feels too heady, it’s worth taking a moment to reflect on whether his feelings are genuine or if he’s using the relationship as an emotional crutch. Sarah, who moved in with her separated partner just two months into dating, realized it the hard way when she began to notice that he couldn’t stop reminiscing about his ex and his marriage. No matter what the topic of conversation, he’d invariably mention his ex, and Sarah started feeling like he wasn’t quite as over her as he’d led her to believe. 

5. He’s emotionally unavailable

walking away from a separated man
Being emotionally distant is a sign he is not ready for a relationship

One of the signs a separated man is ready to date is that he is emotionally available and vulnerable with his current partner, which serves as the foundation of a strong relationship. On the flip side, difficulty opening up, avoiding deep conversations, or being distant during emotional moments are red flags when dating a separated man. 

These are clear indicators of emotional unavailability, which stems from not having fully processed the breaking up of his marriage. “Emotional unavailability is common among recently separated individuals,” says Dr. McCarthy. “They may need time to heal before they can fully open up.” 

6. He avoids talking about the future

If he’s reluctant to discuss a future with you or talk about where the relationship is heading, it could mean that he is not ready for commitment or perhaps, hasn’t fully shut the door on the possibility of a reconciliation with his wife. If every time you bring up the topic of going away for a vacation, exchanging keys to each other’s houses, or meeting friends or family, your partner deflects, it surely means he’s unsure or hesitant to move forward. “A man who sidesteps future plans might not see you as a long-term partner,” warns Ava Torres. 

Related Reading: 15 Signs A Commitment-Phobe Loves You

7. He’s still financially tied to his ex

Financial obligations like joint accounts, shared debts, or ongoing alimony disputes can become a source of friction because they create stress and limit his ability to focus on building something new with you. Besides, when you find your partner splitting bills or managing joint debts with his former spouse, it can leave you wondering, “Is he still married to her in his mind?” 

This can bring a whole lot of other insecurities in the relationship. While such financial entanglements aren’t always avoidable in the dissolution of a marriage, you need clarity on whether your partner has a plan and a timeline for resolving these. If not, it’s a definite red flag that will impact your relationship sooner or later. 

8. His kids aren’t aware of you 

If you have been together for a considerable amount of time and he has been talking about commitment and exclusivity but is hesitant to introduce you to his children or keeps your relationship secret, it’s a red flag that he may not be prepared to put his money where his mouth is. 

“Keeping you a secret from his children may suggest he’s unsure about the relationship’s seriousness,” says Dr. McCarthy. While taking time to introduce a new partner to children is wise, complete secrecy might indicate that he’s not ready to blend his old life with his new one.

9. He compares you to his ex

walking away from a separated man
Comparisons mean a part of him is still hung up on his spouse

Speaking of red flags when dating a separated man, this one takes the cake because of just how hurtful or invalidating it can be. Whether positive or negative, comparisons to an ex are a sign that he’s still mentally preoccupied with his past relationship and can make you feel like you’re competing with someone who isn’t even present.

Statements like “You’re so much more understanding than my ex” or “I could never open up to my ex the way I can with you” can seem flattering at first, but if you really think about it, it means that he hasn’t been able to make peace with the past and a part of him is always thinking about his ex. Perhaps, he is using this relationship with you to validate his choice of walking away from his marriage. 

10. He avoids introducing you to his friends and family

While it is understandable for a man dating while separated from his wife to take things slow in his new relationship, if you have been together for several months or even a year or more and he still hasn’t introduced you to his family or brought you into his social circle, it’s a red flag that he is either unsure of the relationship or self-conscious about his decision to start dating before his divorce has been finalized. 

Either way, this hesitation means that he isn’t ready to fully integrate you into his life. “This could indicate he’s not ready to make the relationship official or is unsure about its longevity,” warns Dr. Summers. The reasons may vary but the bottom line is that if he is dragging his feet on welcoming you into her inner circle of people, he has his doubts about this relationship and it’d be wise for you to not pin your hopes on it working out for the long haul. 

Related Reading: We Couldn’t End Our Relationship Nor Do We See A Future Together

11. He’s still very involved in his ex’s life

While co-parenting or shared responsibilities can necessitate some level of contact with his ex, excessive interaction might indicate lingering emotional ties. If he is keeping tabs on whether or not his ex is dating and whom, checks in to see if she is doing okay, goes out of the way to support her if she is unwell or emotionally low, these unhealthy boundaries with his ex are a clear warning sign that he may still have feelings for her. This lingering attachment can hinder your ability to build a relationship on your own terms.

9 Tips To Navigate Dating A Separated Man

If you notice any of the glaring red flags when dating a separated man, my recommendation would be that you cut your losses and walk away. Someone who hasn’t taken the time to close an important chapter of life, mourn its loss, work through the grief, and reflect on how to grow from the experience can never be the partner you deserve. Besides, all that drama comes from unresolved relationships and emotional tanglements is just not worth it. 

Even if he’s done what it takes and shows all the signs a separated man is ready to date, there may be emotional and logistical complexities that can affect your relationship with him. That’s why dating a separated man requires careful navigation. Here are some expert-backed tips to help you manage this dynamic effectively.

1. Understand his separation status

issues with dating a divorcee
A conversation about his separation is crucial for understanding if he is ready for a new relationship

It’s essential to clarify where he stands in the separation process. Is he newly separated, or has it been a while? Is the divorce finalized? These details can indicate how ready he is for a new relationship. Dr. Summers explains, “The separation timeline matters because a man who’s recently separated may still be processing emotions like grief, guilt, or anger.” To truly understand where he stands vis-a-vis the separation, you mustn’t hesitate to ask questions like, 

  • What has this separation been like for you so far?
  • Do you feel ready to move on?
  • With all that’s going on in your life, do you think you can make space for a new relationship?
  • Are you sure the separation is permanent or do you think there is scope for reconciliation?

 This will give him a chance to share his emotional state and the logistics involved.

2. Set clear boundaries

Setting clear boundaries is crucial when dating a separated man to define the relationship and ensure you’re not pulled into unresolved issues such as his interactions with his ex or co-parenting responsibilities. “Boundaries are crucial in ensuring you feel respected and secure while he navigates his separation,” says Ava Torres.

For instance, if his ex calls or texts any time she needs to discuss something about the children and it bothers you that it eats into your quality time together, discuss prioritizing your time together. You could put your point across gently by saying something like, “I understand you have commitments, but I’d like us to create uninterrupted time for each other.”

Related Reading: 9 Examples Of Emotional Boundaries In Relationships

3. Take it slow

As we’ve discussed, rushing into a relationship might indicate that a separated man is monkey-branching to avoid dealing with the emotional pain or using you as an emotional crutch to get through a difficult time in his life. That’s why, if you feel like he’s taking things forward at a pace you’re not comfortable with, insist on slowing down the relationship

Dr. McCarthy advises, “Pace the relationship in a way that feels natural and allows space for both of you to address your emotions honestly.” This will allow you to build trust and gauge compatibility. You can do this by setting small milestones like meeting his close friends or having a conversation about exclusivity only when both of you feel comfortable.

4. Evaluate his emotional availability

A man who is separated from wife may still be hurting and not be emotionally ready to invest in a new relationship. Before you get too emotionally invested, look for signs a separated man is ready to date such as his ability to communicate openly and handle conflict maturely.

Notice how he responds to emotional conversations. If he avoids them or shuts down, it may indicate he’s not fully ready. That’s your cue to reassess how much you want to invest in this relationship. 

“Emotional availability is about being present and engaged in the relationship. If he’s emotionally distant, it’s a red flag.” 

—Dr. Anita Foster, psychologist 

5. Avoid being a rebound

If he’s dating to distract himself from pain or loneliness, you risk becoming a rebound. A rebound relationship can feel intense at first but often lacks long-term stability. Dr. Summers warns, “Be cautious of relationships that move too quickly or feel like they’re based solely on physical or emotional dependency.” To make sure you don’t go down this rabbit hole of emotional pain: 

  • Look for depth beyond initial chemistry
  • See if he is ready to invest in the relationship
  • Ask about his dating goals 
  • Ensure they align with yours

Related Reading: Do Rebound Relationships Ever Work?

6. Be prepared for baggage

No matter how much time and effort he has invested in working through his emotional struggles and healing from the setback of a marriage not working out, there is bound to be baggage. Apart from emotional baggage, there is also logistical baggage involving ongoing legal matters, co-parenting, or financial ties. 

You have to be mindful that these factors can impact your relationship and be prepared to offer support to your partner. “You don’t have to fix his problems, but you should be prepared to navigate the complexities that come with his situation,” says Ava Torres. For instance, if he’s dealing with child custody arrangements, be supportive but also assertive about how much involvement feels comfortable for you.

7. Respect his co-parenting responsibilities

If he has children, they will understandably be a top priority. However, this doesn’t mean your needs should be sidelined. For that, you need to discuss schedules and set relationship expectations early on, honestly and maturely. For example, talk about, 

  • How you will handle time for each other when it’s his turn to have the kids 
  • When he’d feel comfortable introducing you to the kids 
  • What kind of role you’re likely to play in their lives 
  • How to handle last-minute changes due to his kids’ needs without creating resentment
More on unhealthy relationship

8. Don’t ignore red flags

Even if things start off smoothly (as they usually do), make sure you pay attention to red flags when dating a separated man as and when they emerge—be it excessive involvement with his ex, avoidance of serious conversations, emotional unavailability, or lack of boundaries with ex. And address them without delay. 

For instance, if you notice that your partner is suddenly too involved in his ex’s life, say, “I’ve noticed you’re talking to and spending time with your ex a lot, and I’d like to understand what’s going on. Can we talk about it?”

Related Reading: Emotional Flooding: What Does It Mean In A Relationship?

9. Prioritize your own emotional well-being

Above all, prioritize self-preservation and safeguarding your emotional well-being. It’s easy to get caught up in someone else’s challenges, but don’t let it eclipse your happiness and emotional health. “A healthy relationship starts with two whole individuals. Don’t lose yourself while trying to support someone else,” says Ava Torres. Set boundaries to ensure you have the time and energy to invest in yourself and prioritize your:

  • Self-care routines
  • Hobbies
  • Friendships
  • Ambitions and goals

Final Thoughts 

Infographic on Red Flags When Dating A Separated Man
Dating a separated man? Watch for these red flags!

Dating a separated man can work if both of you approach the relationship with honesty, patience, and emotional readiness. By setting boundaries, taking it slow, and prioritizing open communication, you can build a connection that respects both his situation and your needs. Above all, trust your instincts—your well-being matters just as much as his.

Being A Second Wife: The 9 Challenges You Should Be Prepared For 

12 Signs His Ex-Wife Wants Him Back (And What To Do)

15 Most Common Reasons For Divorce

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