Finding Love Again: A Remarried Widow's Guide to Opening Your Heart After Loss

Finding Love Again: A Remarried Widow's Guide to Opening Your Heart After Loss

When grief enters your life and takes your spouse, the idea of loving again can feel impossible. Yet thousands of widows eventually find themselves wondering if their heart has room for both honoring the past and embracing a new future. The answer, as Connie Gilmore-Dizard and her husband Chip reveal in their powerful story, is a resounding yes—but it requires intention, patience, and a special kind of person willing to walk alongside you.

The Journey from Widow to Wife Again

Connie's late husband passed away in June 2014, leaving her to navigate life as a single mother while carrying the weight of profound loss. By the time she met Chip seven years later in late 2020, she had reached a pivotal place in her grief journey. She wasn't desperately searching for someone to complete her—she had already learned to stand on her own.

"I got to a place where I was kind of set in my ways," Connie shares. "Once I get my daughter out of high school, I'm just going to do me. I didn't meet Chip and say, 'Oh my God, that's my husband.' I met him and thought he was a really nice person."

This mindset shift is crucial for widows considering dating again. Connie had moved beyond the desperate need for companionship and into a space of contentment with herself. She knew her worth and wasn't willing to settle for anything less than what she deserved.

The Power of Being Clear About What You Are

One of the most impactful moments in Connie and Chip's early relationship came when Connie made a bold declaration: "I'm a wife."

But she was careful to clarify: "I didn't say I'm your wife. I said I'm a wife. I may not be your wife, but I am a wife."

This distinction matters profoundly. Connie was communicating her identity and standards without pressure or presumption. She was letting Chip know that she wasn't interested in being a long-term girlfriend or playing games. She had been a wife before, knew what that meant, and wouldn't accept anything less than that level of commitment—whenever she found the right person.

For widows navigating the dating world, this approach offers a powerful framework. You're not auditioning to be someone's wife. You're allowing someone the opportunity to prove they're worthy of the wife you already are.

What Makes Someone Special Enough to Date a Widow

"It takes somebody very special to date a widow," Connie explains. "They have to have certain characteristics. They don't necessarily know that they have these characteristics, but they just have to come with a certain heart."

Chip didn't have a playbook for dating a widow. He was divorced, not widowed, and had never been in a relationship with someone carrying this particular kind of grief. But what he did have was curiosity, compassion, and a genuine desire to understand the woman he was getting to know.

"If a guy or man really wants to spend time with you or get to know you, he will," Chip shares. "I was just very interested in learning her and learning her past and seeing how amazing she is. It was just a natural thing for me. There was no playbook. I couldn't call a friend or Google it. I just learned to be there."

The Cemetery Visit That Changed Everything

Six months into their relationship, the anniversary of Connie's late husband's death approached. In a move that would prove transformative, Chip offered to drive Connie to the cemetery.

"Nobody had ever asked me that," Connie recalls, her voice still filled with emotion years later. "I couldn't even imagine anybody being in that space to even do that."

What happened next revealed the depth of Chip's character. He drove her there but never left the car. He didn't try to look at the headstone or insert himself into that sacred moment. He simply stood by the car, giving Connie space to grieve while making sure she knew she wasn't alone.

"He gave me a hug when I came back to the car and said, 'I'm here for you,' and that was it," Connie shares. "That day told me a lot about him. There's something really special about him."

This moment exemplifies what widows need from partners: presence without intrusion, support without pressure, and the understanding that they're not competing with the past—they're honoring it alongside their partner.

The Reality Check: Dating as a Widow Isn't Easy

Before meeting Chip, Connie experienced what many widows know all too well: dating after loss is complicated and often frustrating.

"The dating pool is strange," she admits. "I remember saying, 'I don't remember dating being like this.' Not only were things different, I was very different. What I was looking for was very different from what I was looking for 20, 25 years ago when I married the first time."

The challenges widows face in dating include:

Partners intimidated by the late spouse: Many people Connie dated were fine at first but became uncomfortable if she mentioned her late husband's name too often or posted about him on his birthday or death anniversary.

Lack of understanding about grief: People expected her widowhood to turn off like a switch once they showed up and were "amazing."

Different life stages and experiences: After years of handling everything alone, widows develop independence and self-sufficiency that can be difficult to adjust in a new relationship.

Protective walls: The trauma of loss often causes widows to build emotional barriers that make vulnerability challenging.

"I wouldn't let him in," Connie says of her early interactions with Chip. "He would say, 'I can't read you. Do you really like me?' It was a level of protection I felt like I needed to give myself."

The Almost-Breakup That Led to Breakthrough

Even Chip and Connie's seemingly perfect love story hit a critical breaking point. While Chip was in Mexico shooting a wedding, Connie had had enough of what she calls "foolishness" and told him she was done. She blocked him on everything.

"I said, 'You have a wonderful trip and a wonderful life,'" Connie recalls.

Chip's response proved everything. The moment he landed back in the United States, he didn't even go home—he went straight to Connie's door.

"He said, 'Tell me exactly what are you going to do different?'" Connie remembers. "And everything he said, he did."

Within 24 hours, they were enrolled in couples counseling. Not the gentle, easy kind—intense, accountability-focused counseling where the counselor didn't hold back.

"The counselor was on him about everything," Connie shares. "I was thinking to myself, 'We're never coming back here.' But Chip took it on the chin, took his notes, did his homework. Every week he kept going, and everything he needed to fix and change, he worked on."

The Transformative Power of Pre-Marital Counseling

Both Connie and Chip credit their eight-week counseling program as essential to their success.

"Had we not done that, we wouldn't be here," Connie states emphatically. "We wouldn't have got married."

The counseling helped both of them see patterns they didn't recognize. For Chip, it meant examining how he presented himself on social media, who he surrounded himself with, and how intentional he was being in the relationship. For Connie, it meant learning to trust again and let go of some of the control she'd needed to maintain as a widow and single parent.

"You gotta trust Chip. You can't be so territorial about everything," the counselor told Connie. "When you lose your spouse and become the sole provider, you take on this role and become very territorial about all your things. You love differently."

Practical Wisdom for Widows Considering Dating

Know Your Worth and Set Boundaries

Connie's declaration that she was "a wife" set the tone for her entire relationship with Chip. She wasn't desperate or willing to settle. She knew what she brought to a relationship and what she required in return.

Don't Rush—Take Your Time

Connie and Chip talked for months before meeting in person due to COVID restrictions. When they finally met, it was in their respective cars with windows rolled down. This slow build allowed them to develop a genuine friendship and emotional connection before physical attraction took over.

Look for Intentionality Over Grand Gestures

"One thing Connie always says about me is that she loves the intentionality," Chip shares. "I plan things intentionally for birthdays, for special holidays. She doesn't have to worry about anything."

This intentionality showed up in small ways too—Chip remembering June 23rd (the anniversary of Connie's late husband's death) and keeping that date clear on his calendar every year, asking "How can I lighten your load?" and genuinely meaning it.

Seek Counseling Before Marriage

Don't wait until problems arise. Connie and Chip's proactive approach to counseling before engagement gave them tools to communicate effectively and address issues before they became relationship-enders.

Honor Both Your Past and Your Present

"Me loving Chip and marrying Chip takes nothing away from the love I had for my late husband or the memories or the grief that still lives within me," Connie explains. "It didn't magically go away on January 14th, 2024, when I became his wife. And when I think about it, I wouldn't want it to."

The right partner will understand that your late spouse isn't competition—they're part of your story and shaped who you are today.

Advice for Men Dating Widows

Chip's perspective offers invaluable insights for men considering relationships with widows:

Find Accountability Partners

"You need someone, preferably another man, who loves you but is not impressed by you," Chip advises. "Someone who can tell you things one-on-one that you may not want to hear but that's going to help you out."

He credits surrounding himself with men who held him accountable for how he treated Connie and represented their relationship when she wasn't around.

Change Your Environment and Influences

As a photographer, Chip's social media was filled with images of female clients and wedding content that made him look single. His counselor challenged him to change that.

"Your social media looks like a single man," the counselor told him. "You need to change who you're around, who you're with, who you're traveling with. Perception feeds reality."

Be Present in the Grief

"Sometimes there's just ministry in presence," Chip reflects. "Being there. I know June 23rd. I don't book anything on that date. That's the anniversary of her late husband's death. That date will never be on my calendar for anything but to be there for her as long as I live."

Ask the Right Questions

Chip regularly asks Connie, "How can I lighten your load?" This simple question communicates care, partnership, and a genuine desire to support her.

Study and Learn

Chip made it his mission to understand widowhood—not just Connie's specific experience, but the broader journey widows face. He listened to her stories, asked questions, and paid attention to how she interacted with other widows through her nonprofit work.

Represent Your Relationship Well

"Once she can trust me with her heart and how I represent her when she's not around—that's what I knew I had," Chip shares. "It wasn't about spending money or doing fancy things. She knows that when I leave her or she leaves me, I represent us well."

Navigating Blended Families After Loss

Both Connie and Chip brought three children each into their marriage, but their situations differed significantly. Chip's daughters could go home to their mother. Connie's youngest daughter, who was only six when her father died, had to adjust to a new family dynamic in her own home.

"For my daughter, she has to learn and get to the place where she feels like it's a bonus, because all she sees is a deficit," Connie explains. "They had him until this age. I was only six years old. There's a lot she missed."

The Plant Analogy

Connie uses a powerful metaphor for blended families: "It's like a plant or a tree that you plant. It's just a little bitty thing, and it takes time—sometimes years—for it to mature to what it's going to be."

She had to resist her natural inclination to force everything together quickly and instead allow the family dynamic to grow organically.

United Front

"One thing we always say together is that we honor each other," Chip states firmly. "Nobody's going to come in between us. We don't care if it's a child, another person, a parent, a cousin. We're here, and we're clear about that."

They have what they call "courageous conversations"—difficult discussions about their relationship, their children, and their blended family that keep them aligned and strong.

Patience with the Process

"When you're coming into a situation, it's not about me," Chip acknowledges. "Seven to ten years, it's just been Connie and her daughter. Everything. And then all of a sudden, she gets remarried. Out of our six children, one child's life is totally different. The other five are not. I have to understand that."

He admits it tests his patience as someone with a "get stuff done" personality, but he's learning that some things can't be rushed.

The Reality of Grief in a New Marriage

One of the most important truths Connie and Chip share is that remarriage doesn't end grief.

"People assume that because I had this wonderful, beautiful wedding that was published and he's amazing, clearly she's all right," Connie says. "That couldn't be more wrong. It's still there. There's still pain."

Even during the week of her daughter's graduation—a joyful milestone—Connie found herself processing grief about what her late husband was missing.

Creating Space for Both Joy and Sorrow

The key to their success is Chip's willingness to give Connie space for her grief while remaining present.

"If I say I'm going to the cemetery, his first question is always, 'Are you okay? Do you need me to come?'" Connie shares. "There are times where I just need that space, and there are times where she may need that, or I'm just having a moment."

Chip understands that Connie's love for him doesn't diminish her love for her late husband, and her grief doesn't diminish her joy in their marriage. Both can coexist.

"I remind people all the time that me loving Chip takes nothing away from the love I had for my late husband or the memories or the grief that still lives within me," Connie emphasizes. "That part of my life shaped me to who I am. It's a strong reminder of the love I had. I'm blessed to have had that love and then to be blessed again to have this love."

Letting Go of Control and Learning to Receive

One unexpected challenge for widows in new relationships is learning to relinquish control after years of handling everything alone.

"As a widow, when you've handled all the things for any length of time, it's hard to let go and relinquish that," Connie admits. "It's not that I don't trust you with it. It's just been my routine. It's also been a safe place I've built."

Chip had to physically stop Connie from doing tasks like taking out the trash and cutting the grass.

"It's autopilot," Chip explains. "I had to say, 'You have a husband now. I got this. I can cut the grass. I can do the trash. I can pay the bills.'"

For widows, this adjustment represents more than just task distribution—it's about vulnerability, trust, and allowing yourself to be cared for again after becoming entirely self-reliant.

Red Flags to Watch For When Dating as a Widow

Based on Connie's dating experiences before meeting Chip, here are warning signs that someone may not be right for you:

Intimidation by your late spouse: If someone becomes uncomfortable when you mention your late spouse or post about them on significant dates, they're not emotionally mature enough for this journey.

Expecting grief to disappear: Anyone who thinks your widowhood should "turn off" because they're in your life doesn't understand grief and probably never will.

Unwillingness to learn or grow: If someone isn't curious about your experience or willing to educate themselves about what widowhood means, they're not putting in the effort you deserve.

Lack of intentionality: If they're not making concrete plans, following through on promises, or showing up consistently, believe their actions over their words.

No accountability: Men (or women) who don't have people in their lives holding them accountable often repeat negative patterns.

Rushing physical intimacy over emotional connection: Take your time building friendship and trust before physical intimacy.

The God-Designed Connection

Both Connie and Chip believe their relationship was divinely orchestrated. From the social media connection to discovering they were literal neighbors without knowing it, the signs of alignment were everywhere.

"God gave me more than I even knew to pray for," Connie reflects. "There were things I didn't even know to ask God for, especially as it related to having someone with the heart for being there. God knew what I needed."

She had prayed for specific qualities in a future spouse, but God exceeded those prayers with things she hadn't even thought to request—like a man who would stand by the car at the cemetery, offering presence without intrusion.

You're Not the Same Person You Were Before

Both Connie and Chip emphasize that they're different people than they were in their previous marriages—and that's not a bad thing.

"I'm not the same person I was decades ago before this happened," Connie says. "I'm a different wife. I'm a different person. I'm a different mother. And my husband sitting here with me is not the husband he was in his past marriage. He's a different man."

Their experiences—her widowhood, his divorce—shaped them into people capable of the relationship they have now. They brought hard-won wisdom, humility, and intentionality that younger versions of themselves didn't possess.

The Challenge of Remarrying After 40

"When you get married or remarried over the age of 40, it's tough," Chip admits. "We're tough. We're set in our ways."

Both brought established routines, independent lives, and strong opinions into their marriage. But they also brought maturity, self-awareness, and a willingness to do the work necessary for success.

"God has shown us both through trials and through hard times and through people in our lives what love is," Chip shares. "He showed me, especially being divorced, that if I made this mistake before, I don't want to repeat the same mistakes twice. So what can I do to be better?"

A Message of Hope

Perhaps the most powerful takeaway from Connie and Chip's story is this: your story isn't over. Widowhood changes you forever, but it doesn't have to define your entire future.

Connie remembers meeting Sophie about a year into Sophie's widowhood journey. Sophie was deep in grief, unable to imagine feeling differently.

"I looked at her and said, 'You're not going to feel this way always,'" Connie recalls. "She told me later that she hung onto those words in her hard times when grief would hit out of the blue."

For widows wondering if love is possible again, Connie's message is clear: it is. But it requires the right person at the right time when you're in the right place within yourself.

Stand your ground. Know your worth. Don't settle. And when it doesn't line up with what you know you want or need, be willing to walk away—even if it's scary.

Because somewhere out there, there may be someone learning to be the person you need, even if they don't know you exist yet. Someone willing to honor your past while building a future. Someone who understands that your late spouse isn't competition but part of the beautiful, complicated, resilient person you've become.

And when you find that person—or they find you—the wait will have been worth it.

Connect with Premature Widow: Learn more about Connie Gilmore-Dizard's nonprofit supporting widows at prematurewidow.org

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