Eight Things To Consider When Dating A Divorced Man

Updated April 1, 2024by Regain Editorial Team
“It is definitely okay and normal to be nervous going into a new situation with new dynamics. Try to validate that while also talking through any concerns that you might have openly and honestly.” - Ryan Smith, LPC, NCC

A lot of the time, dating pools are filled with single individuals who just haven’t found what they’re looking for yet. Other times, you might come across people who have been in longer-term relationships but called them off for various reasons. In some cases, you might meet someone who has gone through with a marriage but is now divorced and back on the market. Dating a divorced man may be different from dating someone who has never been married before, but every situation is different. Being aware of what to expect when dating a divorced man can help you assess whether you’d like to get into and proceed with this kind of relationship.  

Do you have questions about dating a divorced man?

1. Divorced dating doesn’t have to lead to nerves

Sometimes finding yourself attracted to a divorced man can be intimidating because it may seem unfamiliar compared to dating around with other guys who have never been in that serious of a relationship before. Remind yourself, though, that some marriages don’t last as long as other long-term relationships do without a set of rings and a piece of paper binding the two partners together. Having a marriage end can mean a lot of different things for various individuals, and it can be nearly the same in many ways as dating someone who has had other relationship experiences besides divorce. 

2. Marriage can mean different things for different people

There are many reasons a person may have been married at some point in their lives. Sometimes people are young and in love and jump straight into marrying someone before they grow older and mature more. By the time they realize that they want different things out of their lives, it may be too late. Sometimes a couple may conceive a child, whether planned or unplanned, and feel that marriage is the next step that they absolutely must take at that point in their lives. Then, they may come to realize that it wasn’t necessary or would not work for them even with a child in the picture and that the two of them needed to eventually part ways. 

Sometimes two people were happily married for a long time, but events took place in their lives that damaged their relationship, and the marriage fell apart and had to be dissolved. Life happens, things change, and being divorced is becoming a common occurrence. In many ways, it doesn’t differ much from someone else who has been in a serious, committed relationship without the marriage title. 

The importance and seriousness of marriage can vary depending upon the individual. Going through a divorce before getting involved with someone new may affect these thoughts and opinions. Plenty of people go through life with numerous marriages and are comfortable with that level of commitment, even when it hasn’t worked multiple times before.

Some people may have been married once and had it end in a divorce but were able to find love again and remarry and then remain happily tied to their new love for the rest of their lives. In other cases, having a significantly damaging marriage leading to a divorce can be so traumatic for some that they vow not to get married again, even if they still plan to find someone to love and spend the rest of their lives with. If you’re planning on entering into a serious relationship with someone who has been divorced, these may be a few things to take into consideration that can affect your long-term plans and goals, as far as the relationship itself is concerned.

3. Dating when children are involved

You don’t have to have been married to have children with someone else, but divorced parents may have a bit more factors to navigate when they want to begin seeing someone else. This is something that can affect a person’s schedule when it comes to free time and may make them more unavailable than someone without children.

Parents can also be very particular about who they want around their kids as well. Although a divorced man may or may not let their child meet someone they are dating before it gets more serious, the ex-spouse may also be capable of having a say in who is “acceptable” to be around their child. Certain behaviors or traits may not be desired for potentially influencing any children involved, and those boundaries need to be respected.

Even if both parents are still involved, it can be difficult (regardless of age) for a child to adjust to their parent moving on or getting involved with new potential love interests. It can be important not to pressure a single parent to involve you in something as serious as being around and made known to their child until they are ready and feel that the relationship is serious enough to let their child know.

Although younger children seem to be more capable of being accepting of their parents bringing someone new around at times, older children may struggle with the idea of their parents being replaced by someone else. Divorce can be hard enough on a child at any age, but they can end up feeling significant resentment once one of their parents chooses to move on and find another relationship. This could be tied to feelings that their other parent is being replaced or stem from jealousy that their father is choosing to allot some of their time to anyone besides them when the children may need their father’s love and attention the most.

4. A divorced man might still be friends with their ex

Jealousy can poison any relationship. Sometimes, it may be difficult to date someone who is friends with a past fling or love interest despite having never been married to them. When the man you’re interested in has been married before, yet remains on positive terms with their ex-spouse, this can be an area of concern if you have certain insecurities. There may be doubts creeping in about if they’re still secretly in love with their ex and you might worry about whether you’d be pushed to the side eventually or may not compare to how close or how serious their relationship once was. While these situations can occur, more often than not, these emotions can stem from a place of unease. Reassurance from the divorced man you’re seeing may help. 

Plenty of divorced couples end up divorced for a variety of reasons, and not all of them are negative; sometimes, the relationship doesn’t work in the long-term, romantic way it was planned to. It can be acceptable and healthy for them to remain friends with their ex-spouse and stay on positive terms, especially if the two of them never had any children involved.

If this becomes a significant area of concern as you date a divorced man and you feel the nature of the relationship has become more serious, try to be gentle in addressing the topic, but express your concerns and ask for reassurance. If they are growing closer to you and are ready to begin a new relationship with you, it can be helpful if they are willing to answer your questions honestly. Being transparent can help you to feel more comfortable with the friendship they may still maintain from their past marriage. 

5. Alimony and financial concerns

One thing that a divorced man may have that a single man may not is legally required financial aspects, such as alimony or child support. A man who’s never been married but has had children with someone else may still find themselves in the position of paying child support to the other parent, but only a divorced man will have to deal with alimony payments.

Although these payments may be based upon their particular income and fit into their current financial structure, it’s something to be aware of if you were to become involved in a more serious nature and stay with them for a long time. This monthly deduction of money from the earnings they make may have an impact on any potential savings or the ability to significantly provide for a future spouse or offspring.

If your dating relationship with a divorced man becomes more serious, and you seem to have a future together that includes living together, getting married, or having children, this is something to discuss with them when the time comes so the two of you can effectively plan how to approach the issue and adjust your plans and financial situation accordingly.

6. Getting divorced may have had an impact on their self-esteem

Sometimes getting divorced and removing yourself from a very unhealthy marriage and relationship can be a blessing, but sometimes it could have also been a situation where one spouse desired to leave, and the other agreed but didn’t truly want it to happen. Short marriages may be easier to bounce back from (although, not always), but for those who were with the same person for a significant amount of time, it may turn their world on its head for a while.

Diving into a marriage and not having it work may cause a man to question their judgment or possibly themselves. In spite of any other significant factors at play in the relationship that ended, they may feel insecure about their appearance or career if their spouse left them for someone “better.” They may feel undesirable and like “no one will want them” due to having been in a relationship that they thought would last and not being able to make it work. If they were with their spouse long enough for the two to have been constantly seen as an item together instead of as individuals, they may even start questioning who they are on their own and outside of that relationship now that it has ended.

When dating a divorced man, keep in mind that the dissolution of their past marriage may have had some effects on their self-esteem and self-image as they adjust to being single again and figuring out who they are outside of that previously defining relationship. They may be unsure of themselves or seem to be fickle about their thoughts, feelings, or interests as they strive to redefine themselves and stand confidently on their own once again. If you’re truly interested and see yourself having a future with this person, try to be as supportive as possible and understanding as they go through changes on their journey of self-discovery.

Do you have questions about dating a divorced man?

7. Are they ready to move on?

A lot of the time, people may start dating and looking for someone new directly after a relationship ends as a way to distract themselves from the disappointment and heartache of a failed relationship. They may only be looking for what’s referred to as a “rebound” or may be ready to start meeting new people and beginning a new chapter to their lives.

A man that’s been divorced might be ready to find someone else if the marriage they left was unpleasant and a relief to be rid of, but sometimes that may not always be the case. Even if they know the marriage is over and they won’t be getting back with their spouse ever again, some men may attempt to date as a means of moving on but are mentally and emotionally not fully ready to commit to another person just yet.

The man you’re interested in may or may not be fully aware of their true feelings on the matter and at what level of moving on they’re ready to proceed forward, so this is an area to take note of and be cautious about if you find yourself getting attached. It may take some time for them to fully be ready to commit to you and let go of the emotions associated with their past relationship. Or the new dating experience may be so positive that they have no problem with starting a new chapter of their life with you. A man might be more ready to start that new chapter if they’ve taken the time to heal and have accessed resources like counseling. However, every situation can vary. 

8. The future with a divorced man

Divorce doesn’t have to have much of a say in how a person’s future will turn out, and a divorced man can find another love and live happily and healthily with them. This can be something important for divorced men to keep in mind, as well as those who pursue them. As with the topics addressed, many possible factors may need to be taken into consideration when getting involved in a long-term relationship with a divorced man. It can be vital to maintain clear, open, and honest communication about any concerns or potential areas of misunderstanding or worry.

If things get serious, be sure to be respectful of their situation, including any connections to their past marriage and any children in the picture. However, still, try to express yourself truthfully so the two of you can work on making the relationship as comfortable and functional as possible. A healthy relationship is a supportive and honest one, and obstacles can be overcome with clear communication, effort, and the will to work at making it last.

Online counseling with Regain

Are you interested in dating a divorced man but nervous about how to approach the situation? Are you a divorced man wanting to get back into the dating scene, but worried about dating after divorce, or struggling with the emotional effects of your previous marriage? Regain has licensed and trained professionals available from the comfort of your own home, and on whatever schedule fits your needs, to offer advice and support through all of your relationship struggles and concerns. You can get the help and guidance you deserve through phone calls, video chats, or in-app messaging and connect in an environment that feels safe to you. 

The efficacy of online counseling 

Online counseling can be an effective treatment option for individuals going through divorce. In a study published by the Journal of Family Psychology, researchers found that an online platform successfully reduced the adverse mental health effects of divorce. This included anxiety, depression, and symptoms of somatization. 


Dating a divorced man can come with unique challenges, but it can also be much like dating anyone else. Every individual comes with different life experiences that make them who they are. By getting to know the man on a deeper level, you can begin to assess whether you’d like to be in a relationship with them. If you’re confused about what you’d like in a significant other or are exploring the possibility of dating a divorced man, speaking with an online relationship counselor could help you find more clarity. 

For Additional Help & Support With Your ConcernsThis website is owned and operated by BetterHelp, who receives all fees associated with the platform.
The information on this page is not intended to be a substitution for diagnosis, treatment, or informed professional advice. You should not take any action or avoid taking any action without consulting with a qualified mental health professional. For more information, please read our terms of use.
Get the support you need from one of our therapistsGet Started
This website is owned and operated by BetterHelp, who receives all fees associated with the platform.