11 Tips for Widows Starting Over in Dating & Relationships

Credit: Style My Soul, www.stylemysoul.com | Widows; Dating and Relationships

Embarking on new relationships can be daunting for widows, but with heartfelt advice from experts, the journey can be made smoother. Style My Soul gathered advice from professionals including a matchmaker & relationship coach and psychologists. Their insights range from focusing on comfort and fulfillment to loving yourself and your body.

Focus on Comfort and Fulfillment
From my coaching experience, the best tip is to give yourself permission to set your own timeline. There’s no set schedule for when to begin dating again, and it’s important to move at a pace that feels right for you. Accept the process of self-reflection to understand what you’re truly looking for in a new relationship. This could mean finding out the qualities you value in a partner or the type of companionship you desire. Yes, starting all over again can be daunting, but by focusing on what makes you feel comfortable and fulfilled, you can go through this new chapter at your own pace and with clarity about your needs and desires. So when you do decide to take those steps back into dating, you’re more likely to build more meaningful connections that align with who you are today. - Bayu Prihandito, Founder, Psychology Consultant, Life Coach for Men, Life Architekture

Embrace the Journey
Embrace the journey of self-discovery. It’s important to take time to understand what you truly want and need in a partner before diving back into dating. For example, consider setting aside a few moments each week for quiet reflection — perhaps through journaling or meditative practices. This can help you clarify your feelings and intentions, making it easier to connect with someone who aligns with your new chapter in life. Remember, the right person will appreciate your journey and the strength you’ve gained along the way. - Hajnalka Nagy, Business Owner | Reiki Healer, Cosmic Self

Give Yourself Permission to Move Forward
My tip would be to give yourself permission to move forward at your own pace and honor your feelings throughout the process. It is okay and normal to feel a range of emotions as you start to open yourself up to someone new. Remember, you are not replacing the love you had; you are making space for a new chapter in your life. Healing and opening yourself to new experiences takes time, so be patient, check in with yourself after each introduction, and trust that the right person will come into your life when you are ready. - Julianne McGowan, Matchmaker & Relationship Coach, Kelleher-International

Grieve with Mindfulness and Compassion
One sincere tip I can share with widows starting over in the dating and relationship realm is to allow yourself time to honor your feelings of grief with mindfulness and self-compassion before gently opening to the possibility of new connections. It is important to take time to reflect, to feel the difficult feelings and the pain of loss, and to make meaning of the loss. Rather than pushing yourself into dating, focus on reconnecting with your own needs, desires, and boundaries, and getting to know yourself again.Healing and self-love create the foundation for meaningful relationships, and it’s essential to take as long as you need to heal, recognizing that your late partner will always be a part of your story.
Be kind to yourself during this process — there’s no timeline for healing or finding love again, and every step you take can honor both your past and your future. - Lauren Korshak, Therapist, Lovewell

Slow Down and Avoid Overcorrection
The two biggest issues I see with widows are intertwined: choosing a partner who is very different from your spouse, and getting married too quickly. I call it “the overcorrection.” If you had no chemistry with your spouse, you overvalue chemistry. If your spouse wasn’t financially stable, you look for money. The problem arises when you find someone who is the opposite and dive into a committed relationship because you’re older. The theory is that you have less time and you’re smart enough to know what you want. Except two-thirds of second marriages fail, and three-quarters of third marriages fail, which means that there are a lot of older people who find partners who seem “better” than their spouses, only to discover that they didn’t date long enough to see their flaws.
My advice: slow down. If you’re widowed, give yourself the grace to date someone for two years before tying the knot. And if that seems like too long, remember: if you’re speeding, you’re more likely to miss your exit.
- Evan Marc Katz, Dating and Relationship Coach for Women, EvanMarcKatz.com

Redefine Your Life on Your Terms
Being ready to date or for a relationship is centered around your healing journey. Part of healing is understanding yourself, practicing self-love, and redefining your life on your own terms. Take about 30 minutes daily for self-reflection, to acknowledge your feelings and progress. Try to dive deeper daily into what makes you feel happy, secure, and valued. Consider what your most important needs and key life values are, such as faith/spirituality, money/finances, family/children, and health/fitness. Communicate these to potential partners early on to determine whether their values align with yours.
Develop a dating blueprint of your ideal partner. Be clear about who and what you want, what your “must-have” qualities are, and know your non-negotiables and deal-breakers. This consistent practice of self-reflection helps ensure that when you do start a new relationship, it’s based on a foundation of true self-awareness and emotional readiness, not just a need to fill a void left by loss. - Avarel Smith, Founder/CEO, Seeking Synergy LLC

Look for Someone with Similar Values
As a therapist and someone who wants the best for you… allow yourself to grieve the first year. You must go into this voluntarily, or else you might not ever do this very necessary, yet difficult process. If you skip it, you could be triggered subconsciously and often in your next relationship. Grief is the part where acceptance, feeling feelings, letting feelings come and go, and hopefulness come into play. My sincerest warning is… many people will try to fix it by introducing you to someone too soon. You might even try to do this on your own. Also, some people prey on vulnerable people and can show you a slanted and very skewed version of who they are, causing more heartbreak in the end. Trauma causes difficulties in executive functioning/decision-making. Give yourself time to heal.
Once you are ready… acknowledge you will not replace anyone, so this will be different. Look for a person with very similar values, rather than interests. Build a friendship first — don’t trust anyone who rushes you. Be interdependent — not codependent. Make sure they have a pattern of positive relationships & behaviors. Trust in patterns, please. Look at your county’s clerk of court website for a history if you don’t know the person. The blessing of dating midlife/older is that we can see patterns of behavior in someone’s life and don’t have to guess. Be realistic in how this person would be around your loved ones if part of your family. Believe love can happen again, but don’t ever settle for anyone who doesn’t share your values. You’ve been through too much already. - Janelle Paris, Founder, Co-Owner, MAEd., LPCC-S, Guiding House

Give Yourself a Full Year
Give yourself a full year to reinvent yourself after fully grieving and reaching healthy acceptance with this significant loss and the major life change that comes with it. People often date too soon and don’t factor in the reinvention phase where you are fully on your own. This is a major identity shift that widows and widowers must go through. Don’t squander the opportunity to step into a new version of yourself. You had your spouse to consider for every decision, and now you’re on your own. It takes some getting used to. Also, for people who were caretakers, enjoy time free from caretaking. You deserve it.
- Lisa Concepcion, Certified Professional Life Coach and Founder, LoveQuest Coaching

Learn About the New You
I’ve been widowed for 12 years. I’ve been a dating and relationship coach for 15 years. When my husband was alive, I only coached divorced people (because I had experienced divorce prior to meeting him). Then Tony died suddenly five years into our marriage, and I suddenly experienced widowhood. After a few years of continuing to coach divorced people, I found a meetup of widowed people through SoaringSpirits.org and learned how important it was to “sit” with people who truly understood my journey. This also opened the door for me to meet widowed people who were struggling to learn how to date in this new world of dating. Most of the widowed people I’ve met were married a lot longer than I’d been — 20, 30, 40, 50+ years — which meant they hadn’t dated often since they were teenagers. And this new world of dating was very confusing and scary for them.
The best tip I can share here for widowed people starting over in the dating and relationship realm is to learn who you are now. Most people feel in the beginning all the things they’re not. Not a spouse, not 20 anymore, not as active, etc. What I suggest is instead to concentrate on all the positive things you are now. Your past experiences that have given you rich emotions, intelligence, experience, compassion, empathy, wisdom, etc. If you find this hard to do, then ask a trusted friend who adores you and will tell you all the truthful positive traits about you. Please write these traits down and don’t edit or delete them. Also, include all the positive traits your late spouse loved about you. Then read them out loud at least twice a day. I suggest doing this before you brush your teeth (it’s helpful to include it with something you already do).
This will help you feel more confident as you venture into making new friends and ultimately venture into dating. Feeling confident will also help you define and confirm who you’d like to include in your future life. This is something I did for myself after Tony died, and I’ve given this as homework to my hundreds of clients, and we’ve all found it helps us feel better about ourselves 100% of the time. - Christine Baumgartner, Expert Dating and Relationship Coach, The Perfect Catch

Honor the Love You Shared with Your Spouse
Remember the love that you shared with your spouse and use that to fuel your new journey to your next love relationship. It is a rare gift in this world to have a wonderful love relationship, and then to be able to share love again at a more mature age: truly priceless! Honor yourself by having the courage to step out on that journey once more.
Honor your loved one who has passed by bringing the love you learned with them, and sharing that love in your next relationship. - Sandy Tomey, Love & Relationship Coach, Sacred Journeys Coaching

Love Yourself and Your Body
One sincere tip I would share with other widows starting over in dating is to truly cultivate self-love and appreciation for your own body. It’s so easy to focus on the loss, the pain, and the changes that widowhood brings, but real love starts within. Reconnecting with myself, my body, my emotions, and my desires has been the foundation for finding love again over the 69 years of my life, not just with others, but with life itself. I’ve learned to honor my body as something sacred, especially after all it’s been through. Taking care of myself, whether it’s through nurturing practices like a relaxing massage, eating food that makes me feel good, or simply taking a moment to appreciate my body in the mirror, has helped me feel alive again. Sometimes heartbreaking experiences cause us to fall into a cycle of self-neglect, and this can deter us from connecting with our ability to feel good about and love ourselves, and to attract the love we desire and want to experience.
By loving myself first, I’ve noticed that I attract more positive and fulfilling relationships, both romantic and otherwise. Starting over in dating has been less about searching for someone to fill a void, and more about stepping into the world with inner peace, confidence, and an openness to whatever new experiences may come. It all begins with how I treat myself. Another heartfelt tip for widows starting over is to embrace vulnerability as a path to healing and connection. In my book, Divine Sexuality, I speak about the importance of being present and authentic in relationships, especially when integrating past experiences into a new chapter of life.
Starting over doesn’t mean forgetting the love that was lost, but rather honoring it while opening up to new possibilities. I encourage my students to tap into deep, sacred self-awareness and to be honest with themselves about emotional needs and desires. When we understand ourselves deeply, this can lead to more authentic and long-lasting connections, as we don’t allow our repressed selves to unconsciously surface and cause strain in our relationships. This can occur when we do not allow ourselves to feel the authentic pain that a heartbreaking experience can bring, and we suppress it. We then expose others or new dating prospects to this unresolved pain. - Ma Ananda Sarita, Founder, Tantra Essence