Should You Date Someone Who Has Been Divorced Twice? 

Approximately fifty percent of marriages end in divorce. Because of this, you may find yourself on a date with a person who was previously married and maybe even married twice. But should you date someone who has been divorced twice?

As a general rule, it is just fine to date someone who has been divorced twice providing they have taken some time to heal from the 2nd divorce, and have done some work on themselves such that they are now better prepared to be in a relationship.

That “work” could be therapy, but it could also be any form of self-help.

However, like any relationship, dating a two-time divorcee can have positive or negative outcomes. There are many factors to consider when deciding to date anyone, including someone who has been divorced twice.

This article will discuss if it’s a red flag for your date to have a past of two divorces, things to consider before dating someone with two broken marriages, and the pros and cons of dating an individual with previous marriage experience.

Is It a Red Flag for My Date To Have Been Divorced Twice?

It’s not a red flag for your date to have been divorced twice unless there are common issues that have gone unresolved and are likely to manifest themselves in your relationship.

Psychologists and statisticians have noticed a common trend among people with multiple divorces. There’s a tendency for continued relationship failures and mental health disorders among this group.

Despite this statistic, you shouldn’t judge a person solely based on past experiences.

People get divorced for many reasons. Your date may have married young for the first marriage and then had a toxic relationship for the second.

As long as your date takes ownership for their failures, works on healing past wounds, and is willing to work on personal growth and commitment in your relationship, the past shouldn’t matter.

If your date has been divorced twice, don’t judge solely on this statement. Pay attention to signs of the actual red flags, such as:

  • narcissistic behaviors
  • lack of emotional connection and involvement
  • emotional issues. 

Your date is likely an excellent partner candidate as long as these red flags aren’t present. 

10 Things To Consider Before Dating Someone Who Has Been Divorced Twice

Starting a new relationship, especially one with the potential to be long-term, is a serious decision. It would be best if you took the time to consider whether or not this person will be a positive addition to your life. It’s no different when determining if you should date someone who has been divorced twice. 

Here are ten vital things to consider before dating someone who has been divorced twice:

1. Children From Past Marriages

If you are thinking about dating someone who has been divorced twice, there are likely children in the picture. Children from previous marriages can put a strain on any relationship.

It would help if you considered whether or not you feel comfortable handling the ins and outs of children from other parents.

The presence of children could also complicate the future of your relationship. Parents care about their children’s opinions, and their ex-spouses will often have a say in who their children can be around.

It’s also worth noting that children tend to be the glue that keeps a marriage together.

People who have previously divorced tend not to work as hard at a relationship that doesn’t include children, especially if they have had children in a previous, broken relationship.

2. Relationship With Previous Spouses

Pay attention to your date’s relationship with the previous spouses.

Acknowledge any areas where healing hasn’t occurred. Do they seem to be over each other? Is there a healthy relationship with boundaries established? If your answer is no to either of these questions, your date may not be ready to enter another steady relationship.

3. Healing From Past Marriage Emotional Injuries

The ending of any relationship comes with emotional injuries.

Because marriages tend to be long-term, serious relationships, the emotional hurts from divorce can be extreme. A promising sign is if your date has undergone counseling or prioritizes self-improvement. A person in denial or angry towards previous marriages isn’t ready to be in a serious relationship. 

It’s also worth looking at how much time has passed since their 2nd divorce.

Healing takes time, and someone who hasn’t taken the time to properly heal is far more likely to be needy or co-dependent and too eager to rush the dating process to turn it into a full-fledged relationship too quickly.

4. Both of Your Religious Views on Divorce

Religion can be an essential aspect of people’s lives. If you or your date are religious, you should consider your religion’s views on divorce and how important it is to each of you to abide by the rules.

For instance, the Catholic Church strictly prohibits divorce, and without a valid annulment, one can’t remarry in the church. Most of the other major world religions allow divorce but discourage it.

These religious teachings could make or break a relationship. It would be helpful to discuss both of your views on this topic before committing to long-term dating.

5. Both of Your Intentions for the Relationship

When entering into any relationship, it’s essential to ensure that both parties are on the same page regarding their relationship intentions. What are you expecting out of this relationship?

Are you hoping for something long-term, potentially leading to marriage, or do you want a fun fling?

Someone with a past of two divorces could desire either option and may feel very strongly about the intention because of the experience of two failed marriages.

If your date has not fully recovered from the emotional toll of divorce, a fling may be the only option. On the other hand, there may be a strong desire for another long-term, permanent relationship.

Discuss your intentions with each other before making your relationship official to avoid any potential misunderstandings and hurts.

6. Financial Concerns

Divorce often takes a financial toll on both sides of the marriage.

If both you and your date are searching for a long-term relationship, it’s worth considering the impact of these financial strains on your relationship. Are you willing to take on these struggles for the sake of your romance with this individual?

7. Behavioral Red Flags

Just because someone has been divorced twice doesn’t mean there’s something wrong with them.

However, there’s a higher likelihood of behavioral red flags in someone who’s had multiple failed marriages than in someone who’s had none.

Here are some behavioral red flags to look out for:

  • There’s a lack of an emotional connection. Does this person show a genuine desire to know you on an intimate, personal level, or is there an apparent emotional distance present?
  • Your date obsesses over the ex-spouses. If all your date talks about is the problems with their exes or seems tormented by reliving the past and hypothetically fixing the previous marriages, you probably shouldn’t enter a relationship with that person.
  • There are clear narcissistic tendencies. A good relationship involves both partners working together to love and support each other. If you feel like you are giving one hundred percent with little to no reciprocation, that is a sign of a toxic relationship.

8. Consistent Areas of Failure in Past Relationships

No one is perfect. We all have our flaws. However, there should be a limit to how lenient we are of others’ faults. 

Take note of the areas that strained your date’s past relationships. Is this person striving for self-improvement? Is there an acknowledgment of past failures and a desire to do better? 

Mistakes are bound to be repeated when someone doesn’t recognize their flaws or has no intention to improve.

9. Your Date’s Self-Confidence

Most people have heard the saying, “you can’t love others if you don’t first love yourself.” Even though it’s a cliche phrase, it holds a lot of truth. 

Take note of your date’s self-confidence and view of self.

Consistent negative self-talk is an obvious sign of low self-confidence. When people struggle with self-confidence, whether that is a result of two divorces or not, they will likely project that mental and emotional state into their relationships. 

10. Your Feelings About Your Date and the Previous Marriages

Don’t forget to trust your gut.

If the fact that your date has had two divorces is a severe issue for you, that feeling is likely to stay. You deserve to feel comfortable and confident in your relationships, so your feelings matter.

Because of the gravity of the past relationships, the ex-spouses will likely be present in your life. Consider how you feel about those individuals and their potential involvement.

Finally, how do you feel about your date and your previous interactions?

Do you feel at peace and secure around the person or on edge? These automatic reactions should hold weight in your decision to pursue a relationship or not.

Pros of Your Partner Having Previous Marriages

The fact that your potential partner has been married twice isn’t necessarily a bad thing.

There are quite a few benefits to the experience of two marriages. Some pros include the experiences your partner has had to learn from, the apparent desire for commitment, and the potential want to work on your relationship.

1. We Learn From Experiences

One upside of dating someone who has been divorced twice is the opportunities that person has had to learn from past experiences. The best way to grow is to make mistakes.

Your partner probably has a wealth of knowledge to pull from to help your relationship thrive. Tools were gathered from mistakes made in the previous marriages and will now be used to strengthen the current relationship between the two of you.

2. There’s an Obvious Desire for Commitment

If someone has been divorced twice, that means they were married twice and may believe that marriage or long-term relationships are important.

This view of permanent relationships can be a promising upside as long as you both desire commitment.

3. Potentially Strong Desire To Work on Future Relationships

Because of past broken relationships, there’s a strong likelihood that your partner doesn’t want another failed relationship.

A strong work ethic and openness to healthy practices, such as couples counseling, could be a package deal with your relationship. You may find that this person can care for you better than they did for their past significant others.

Cons of Your Partner Having Previous Marriages

It would be naive to pretend that someone with two divorces doesn’t come with baggage. Just as there are benefits to these past experiences, there are downsides. Some cons could be emotional scars, the complicated dynamics between the children and past spouses, and an unwillingness to change.

1. Emotional Scars

Broken marriages result in a lot of hurt and emotional scars.

It takes many months or years of counseling to work through these painful interrelationship dynamics. If your partner hasn’t undergone the proper healing work, they probably carry and project many emotional scars into relationships.

2. Complicated Relationship Dynamics

The probability of your partner having had children from the previous marriages is high. Because of this, you need to be prepared for some complex interrelationship dynamics.

Balancing children and co-parenting with an ex-spouse is a tricky dance.

When you add a new relationship into the picture, it complicates things a little more. Your partner will have to determine your role in the lives of the children, and especially in the beginning, you’ll need to respect the decision.

Your date should inform you of any children in the picture and complicated relationship dynamics before committing to a serious relationship. This awareness will help you determine if you’re ready to take on the challenges and responsibilities of dating this individual.

3. Unwillingness To Change

Many people with multiple divorces have an unwillingness to grow and change. This tendency is often the cause of their broken relationships.

Even though this fault isn’t found in every divorcee, it seems to be a common problem. Your partner may have some consistent flaws that are red flags for a healthy relationship. If there’s an unwillingness to grow or work on those areas, you may be at risk for a toxic partnership.


You can date someone who has been divorced twice. However, like with any partnership, you should look out for any red flags that signal a toxic relationship.

Just because someone has been divorced twice doesn’t mean they aren’t capable of having a healthy, successful relationship. Every person has a different story, and these past experiences can often bring more pros than cons to a relationship.

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