Dating and Marriage

Widowed in Their 20’s, Two Meet to Find Love Again — Jessica and Jordan Story

Life can be crazy and unpredictable in amazing ways. Jessica and Jordan experienced tragic losses and found love again.
Published on Jun 25, 2013


10 Dating Tips for Widows and Widowers

An Excerpt from Dating a Widower
Read Chapter 1

Chapter 10
Ten Dating Tips for Widows and Widowers

I’m including this section of the book specifically for any widowers who might be reading it. Dating again after the death of a spouse can be an awkward experience. It can bring out feelings of guilt or betrayal in the widow or widower. It can also bring out feelings of confusion and concern from friends, family, and those who were close to the deceased spouse.

For those who have lost a spouse and are looking to date again, here are ten tips to help you successfully navigate the dating waters.

  1. When you decide to date again is up to you
    There’s no specific time period one should wait before dating again. Grieving and the process of moving on is something that’s unique to each person. Some people take years, others weeks, and then there are those who choose never to date again. Whatever you do, don’t let others tell you you’re moving too fast or waiting too long. Make sure it’s something you’re really ready to try before taking that step.
    I started dating five months after my late wife died. Too soon? There were some friends and family who thought so. But five months was when I felt ready to at least test the dating waters. And though it took a few dates to get the hang of things, I have no regrets about dating that soon.
  2. Make sure you’re dating for the right reasons
    If you feel like dating again, take some time to understand why you have this desire. It’s not wrong to date because you’re lonely or want company. Single people date for those reasons too. However, if you’re dating because you think it’s going to somehow fill the void or heal the pain that comes from losing a spouse, it’s not going to happen. Dating does give you the opportunity to open your heart to another person and the chance to experience the unique and exquisite joy that comes with falling in love again.
  3. Feeling Guilty Is Natural—at First
    The first time I went to dinner with another woman, I felt like I was cheating on my late wife. As we entered the restaurant, I was filled with feelings of guilt and betrayal. Throughout our entire date, I kept looking around to see if there was anyone I knew in the restaurant. I thought that if someone saw me out with another woman, the first thing they’d do was run and tell my dead wife what I was up to. It sounds silly, but I couldn’t shake that feeling the entire evening. A week later, I went out with someone else. The same feelings of guilt were there, only they were less intense. It took about five dates before the feeling went away entirely and I could actually enjoy the company of a woman without feeling guilty.
    As you date, feelings of guilt should subside over time—especially when you find that special someone. If the guilt’s not subsiding, you might not be ready to date again. Give dating a break and try it again when you might be more up to the task.
  4. It’s Okay to Talk About the Deceased Spouse—Just Don’t Overdo It
    Unless you’re dating someone you knew previously, and they are already familiar with your late spouse, he or she is naturally going to be curious about your previous marriage. It’s okay to talk about the spouse when you’re first dating someone. Answer questions he or she may have about your marriage, but don’t spend all your time talking about the dead or how happy you were. After all, your date is the one who’s here now. And who knows—she might make you incredibly happy for years to come. Constantly talking about the past may make it seem like you’re not ready to move on and start a new relationship. Showing a genuine interest in your date and getting to know her wants, interests, and dreams goes a long way you’re ready to start a new life with someone else.
  5. Your Date is Not a Therapist
    Would you like going out with someone who constantly talks about issues she’s having in her life? Dating isn’t a therapy session—it’s an opportunity to spend time with someone else and enjoy their company. If you find yourself dating just to talk about the pain in your heart, how much you miss your spouse, or tough times you’re going though, seek professional help. Spending $60 an hour on professional help will do you much more good than spending the same amount of money for dinner and a movie. Besides, your date will have a more memorable night if it’s about him or her rather than about everything you’re going through.
  6. It’s Okay to Make Mistakes when You’re Finding Your Dating Legs
    When I started dating again, it had been seven years since I had gone out with anyone other than my wife. Because I had a certain comfort level with her, I often found myself forgetting proper dating etiquette, such as opening the car door or walking a date to her door when the date was over.
    If you find yourself forgetting simple dating etiquette, don’t worry about it. Most dates will understand if they know it has been awhile since you dated. But don’t make the same mistakes over and over. Learn from them and continue moving forward. You’ll be surprised how fast your dating legs return.
  7. Defend Your Date
    When your family and friends learn you’re dating again, they may not treat this new person in your life very well. The mistreatment may come in the form of a cold shoulder at family activities or constantly talking about the deceased wife in front of the date. If you have family and friends who are doing this, they need to be told privately, but in a loving manner, that this behavior is not acceptable. If you wouldn’t let family or friends treat your spouse that way, why would you tolerate that behavior toward someone else—especially when your date could become your future spouse? Don’t be afraid to defend your date. If you can’t do that, then you have no business dating again.
  8. Not Everyone Will Understand Why You’re Dating Again
    There will always be someone who will not understand why you’ve chosen to date again. They may give you a hard time or have some silly notion that widows and widowers shouldn’t fall in love again. Their opinions do not matter. All that matters is that you’re ready to date again. You don’t need to justify your actions to them or anyone else.
  9. Take Things Slow
    The death of a spouse means losing intimate physical contact. After a while, we miss the kisses, having someone’s head resting on our shoulder, or the warm body next to us in bed. This lack of physical and emotional intimacy is enough to drive a lot of people into the dating scene. Don’t feel bad if you find yourself missing these things. It’s completely normal.
    In the dating world, wanting something that was part of our lives for years can become a ticking time bomb. It can force us into a serious relationship before we’re ready. The result: a lot of broken hearts and emotional baggage.
    If you’re on a date and it’s going well, don’t be afraid to take things slow. This isn’t always easy. Sometimes it’s hard not to throw ourselves at our date because we want to be close to someone again. We want that warm body next to ours and to have the words “I love you” whispered in our ears. But it can save you and your date a lot of emotional heartache if you wait to make sure what you’re doing is because you love the other person, and not because you miss the intimacy that came with your late husband or wife.
  10. Make Your Date Feel Like the Center of the Universe
    It’s a basic dating rule, but it’s often forgotten by widows and widowers. Because we already had someone special in our lives, it’s easy to forget to make our date feel special too. Treat your date in such a way that he or she feels like she’s with a man who’s ready to move on. She shouldn’t have to compete against a ghost—even if you only have one date with that person. As long you’re out together, she should feel special.
    Even though dating can be awkward and difficult at times, it can also be a lot of fun. There’s no reason being a widower should hold you back from enjoying a night out. Part of the reason we’re here is to live and enjoy life. And dating is a great way to start living again.

Dating a Widower Advice

Written by Todd, a remarried widower
©2008 Used with permission

Hi Michele,

It would be helpful to know from what his wife died and how long she suffered. I have learned that a surprise death is harder to cope with than a prolonged death.

It would also be important to know that he has had counseling to try to sift through his feelings.

As for me, I am still sad that Judy died, as I am (to a lesser but still profound extent) that my grandparents died. But while still sad and missing so many aspects of her and our life together, after 5-1/2 years of a roller coaster ride fighting cancer and having her attention directed away from me and toward her fight and the kids and her losing her desire for me, I grieved losses along those years and have since then wanted a new exceptional wife and mom. I never felt that I was cheating on Judy by falling in love again –but I heard a widow once say that to me, so I am sure it may sometimes be a peculiarity of being widowed.

I know there are books about dating widowed people–I would recommend that you read one. At least one of them wrote about the strangeness of almost having a ghost in the room–can you love a man who will always miss his wife, with whom he was in love and about whom he still needs to talk? (You will need to). That said, you know you are getting a man who loved his wife. The important thing is can he expand his heart and love two great women over his lifetime? (I think this is pretty cool).

I am happy for you. If you love him, take the time and effort to work through these things together. But I would be careful about his feelings of cheating–you need a Song of Solomon marriage for a change and he needs to feel great about the second great love of his life.


Dating a Widow Advice

The widowed are vulnerable when it comes to dating. Our hearts have suffered pain beyond comprehension. In this heart-felt letter, written to Jim, I shared my heart about widows and my fierce intent to protect Christine, a young widow who lost her son and husband in one tragic moment in time.

I share this letter, with you, my friends, in hopes that you will understand the important responsibility for those dating a widow.

While the letter is written from a faith-based perspective, much of the content is applicable to all.

A Letter to You, Dear Friend on Dating a Widow:

By Michele De Santis
2013 Used with permission

I am excited for you to meet____________________. This is an incredible opportunity. Really. Incredible.

She is more beautiful in person than in the photos you saw. Her heart and soul are reflected in her eyes. I believe that people who have experienced the brokenness that comes from losing a spouse have amazing inner beauty and it reflects through their eyes… I have seen it before.

The circumstances of how she lost her husband are tragic. It was an accident. She also lost her only child. She was a stay-at-home mother – loving her family and her life. Her world as she knew it ended almost three years ago… She will eventually confide in you and tell you all the details, if she feels safe and if she feels you are worthy.

She, like many of us, is working to re-build her life – developing new goals and dreams. It is okay not to have traditional goals and dreams – to which you might be accustomed. You see, she knows that God can have other plans. Life has not been an orderly process and she has seen the best laid plans removed from her life in an instant.

Both of you will need patience. The payoff for your patience will be more than worth it, I promise.

We widows are quite different than divorcees. Scripture tells us to protect and care for the widow… in all ways. You will have an awesome responsibility.

She has only gratitude and love for the opportunity to have been married to her husband and to have had such an amazing son.

I believe that she is emotionally healthy enough for an exceptional relationship.

I recommend reading a book on dating a widow. The good news is that a widow or widower can expand their hearts to love more than one great person in a lifetime. If you always remember this, it will help. She will want to talk about her husband and son, at times, and you will need to be able to listen and allow her to speak of them – without feeling threatened or needing to solve a problem. You will need to listen and provide comfort.

There is more good news: You will have someone in your life that will speak highly of you and appreciate you more than you can imagine. This is an amazing gift – one that you would find one in a million times. I am sincere in this.

If you can love her unconditionally, encourage her, treat her like a lady at all times etc. this relationship could be your greatest gift in your life. Of course, I am assuming that there will be mutual chemistry, common beliefs, values, etc…

If you need advice, ever, on dating a widow, I can put you in contact with a friend – a man from Minnesota. He is a strong Christian and widowed. He married a widow and has valuable insight.

From my perspective, to have found you is a gift – and to have listened to my intuition and connected you two is God’s work.

I am praying for you both. I really hope this works. She is an amazing woman.

My expectations are high. I trust and I am hopeful that you are caring, compassionate, kind, loyal, monogamous – a gentleman of gargantuan magnitude. She deserves to have a spectacular life; as do you.

If you are controlling, abusive, have an addiction, or have a history of infidelity / playing women, etc… it would be wise to back out of this immediately. She cannot be hurt – it would set her back in her healing and it would be wrong on so many levels. I say this to underscore the importance I feel in helping her find a worthy partner.

My intent is not to scare you or insult you – I am just working to be very clear and to insure that she is respected and protected.

So please, go forward with this information and be the man God intended you to be. I wish you well and hope that this connection is a beautiful one that nurtures both of you.

In trust,


*Jim and Christine are now married!

Abel Keogh’s Books

dating-a-widowerDating a Widower: Starting a Relationship with a Man Who’s Starting Over

Are you thinking about dating a widower? Your new relationship will have unique challenges you won’t find when dating single or divorced men. For it to work, the widower will have to put his feelings for his late wife to the side and focus on you. But how do you know if he’s ready to take this step?

Drawing on his own experience as a widower who’s remarried, Abel Keogh gives you unique insight into the hearts and minds of widowers, including:

  • How to tell if a widower’s ready to make room in his heart for you
  • Red flags that may indicate he’s not ready for commitment
  • How to handle family and friends who aren’t supportive of the widower’s new relationship
  • Tips for dealing with holidays and other special occasions

Dating a Widower is your 101 guide to having a relationship with a man who’s starting over. It also contains over a dozen real life stories from women who have gone down the same road you’re traveling. It’s the perfect book to help you decide if the man you’re seeing is ready for a new relationship—and whether or not dating a widower is right for you.

marrying-a-widowerMarrying a Widower:

What You Need to Know Before Tying the Knot

Are you in a serious relationship with a widower? Are you considering tying the knot? Any lasting relationship takes a lot of work, but a successful marriage to a widower requires the ability for both of you to work through unique issues that most couples don’t face. Are you up to the challenge?

Drawing on a decade of experience as a remarried widower, Abel Keogh gives you unique insight into what it takes to make any long-term relationship with a widower successful, including:

  • How to make sure your marriage is new, exciting, and fresh instead of a rehash of the widower’s previous relationship.
  • Suggestions and tips for making sure both of you can talk about the late wife, his grief, and any other widower-related issues.
  • What role, if any, the late wife’s family should play in your relationship.
  • How to make the home feel like yours instead of theirs.
  • Ten real-life stories from women who are engaged or married to a widower.

Marrying a Widower will help you decide whether or not the widower you’re dating is prepared to make the ultimate commitment. More importantly, the book will walk you through many of the challenging circumstances that come with tying the knot and help you decide if taking this step is right for you.