Three Dating Dilemmas from Women in Midlife and Beyond

Dating dilemmas

I’m answering your dating dilemmas: how to meet men IRL, how to end the comparison trap, and what to do when you have different future goals.

Here are three questions I received recently, along with the highlights of my answers. You can find the full answers on YouTube below.

Dating Dilemma #1: “Are the best matches not on dating sites?”

Karen, 65, keeps meeting men who are “nice enough” on the apps, but the connection isn’t there. Wonderful matches can come from many places, and dating apps are one avenue for meeting men you would never run into from your couch. Some of those nice-enough men may grow on you if you give them a second or third date, since first dates are often a poor window into who someone really is.

I encouraged Karen to widen her circle. Friends who know her well can become great matchmakers once they hear what she is looking for. Classes, volunteering, travel groups, and events for singles over 50 put her in the company of people who share her interests, and meeting someone while doing something you love lets you see how they show up in real life. A fresh look at her profile and messaging could help too.

Dating Dilemma #2: “He treats me like a queen, but I want to be married and he doesn’t.”

Cheryl, 65, has spent three years with a 71-year-old widower. They laugh, travel, and never fight, and after a 22-year abusive relationship, it is the best partnership she has known. She wants to remarry. He does not, and he is heartbroken at the thought of losing her.

My suggestion was to start by asking him what marriage means to him and listening for what sits underneath his answer. For many widowers, remarrying can feel like a betrayal of a late wife and her family, and it can also involve finances or a fear of losing you. Then Cheryl can share what marriage means to her, whether that is public commitment, security, or the feeling of choosing each other for life. Sometimes the conversation opens a middle path, such as a commitment ceremony or legal agreements that create the security she wants.

If his answer stays the same after an open conversation, Cheryl gets to decide whether this is a true deal breaker. A timeline for that decision can bring peace, because she can stay present with him while she waits for clarity. His sadness shows how much he loves her, and she can hold compassion for him while still moving toward what she wants.

Dating Dilemma #3: “When do we stop comparing a new partner to the last one?”

Allison dated someone for five months after a seven-year relationship ended, and he does everything she wished her ex would do. She is finding it hard to see the big picture.

The comparison trap is common. Your brain uses your ex as the default template for every new person, so a new date gets measured against memories of what went wrong or right before. To make it work for you, write down what you loved about how your last boyfriend treated you and what you felt in your body around him. Then add what you want in a partner as a whole person, including values, humor, curiosity, and how you want to feel at the end of a day together. That list becomes a compass that belongs to you.

Allow yourself time to grieve, even after a five-month relationship, and ask what the chapter taught you about what you need. When you are ready to date again, notice the comparison when it shows up and remind yourself that each new person is a clean slate. Staying curious about who someone is lets connection unfold at its own pace. You also now have a clearer picture of what care and warmth feel like, so you can say yes sooner to people who offer them and walk away with confidence from those who can’t.

Full Dating Dilemmas on YouTube here:

 You can send your dating challenges through my Dating Dilemmas feature at https://tinyurl.com/datingdilemma, and I may answer your question on the blog or the podcast.

If you’re feeling stuck in dating and relationships and would like to finally find love, apply for a complimentary 30-minute love breakthrough session with me https://lastfirstdate.com/application

Women only: Join the “Your Last First Date” Group on Facebook https://facebook.com/groups/yourlastfirstdate

Are you really ready for the relationship you want? Take my Free Quiz https://lastfirstdate.com/dating-relationship-readiness-quiz/ 

Get my books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love and Love at Last: True Stories of Falling in Love Later in Life



from Last First Date https://ift.tt/UDHlEM8

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