[sunny]

50 y/o female. Never been married, Last relationship was 16 years long. It should have only lasted 6 years but I tried to give it a chance and work through the ups and downs. We just weren’t well matched and drafted apart over the years. In the past, I commonly experienced interest in men (or they were interested in me) and it wasn’t reciprocal, so I didn’t date a lot. Now that I’m older and overweight, not young and beautiful (when I was young I was average and plain looking, never beautiful) and it seems like I will never find the right match if I haven’t by now, unless I try to find someone 15 years older perhaps, but I want to be with someone my own age because I’m not attracted to older men . I should have dated one good friend who was interested in me 20 years ago. That is one of my biggest regrets – saying no to a wonderful man 20 years ago for a silly, cultural, and superficial reason – 4-5 inch height difference. We lost touch over the years, so I can’t reconnect with him. I have never met anyone else like him since and he likely married someone else. Although I am well educated, my career never really took off as I had planned and I’m not financially stable. Most single men my age are divorced and some don’t want to remarry, or think women only want to take their money. I’ve always wanted to be financial stable on my own terms but life didn’t turn out that way and I think men might worry I’m after their money, which is far from the truth. How should I go about finding my life partner? I just want to be with the right person who I can feel safe with, be completely myself with, my equal and my partner in life. But I think most men prefer younger, prettier, and could see my lack of money as a red flag that I might want to take their money, although I live a simple life and don’t require a lot to be happy beyond security and stability, good health and good friends, and an occasional vacation, nothing extravagant. Any suggestions for me?

[Sally]

You sound like the kind of woman who deserves something real. I’ve watched my mom go through this. She thought she was done with love, then met someone who adored her exactly as she is. You’re not too late. You’re just at the part where you know what actually matters. Maybe that’s when love finally sticks.

[Mia Caldwell]

It’s not too late to find love it just looks different now. Focus on real connection, not perfection. Join places or apps for people your age who want something genuine. Be honest about who you are and what you want.

Let go of regrets from the past what matters is staying open now. You have experience, kindness, and depth those are things good men value most.

[PassionSeeker]

You’re concerned about your age, looks, and financial situation, but those things are only a fraction of what truly makes a connection lasting. Sometimes, taking risks whether it’s reaching out to old friends, trying new dating platforms, or being more open with strangers can open doors to relationships you didn’t expect. Sometimes the most meaningful connections happen when we challenge our own limitations. Don’t limit your opportunities by only looking at things from a pragmatic lens. You’ve got a lot to offer, and someone out there will value your honesty, kindness, and commitment to living a fulfilling life.

[Nina A]

You don’t start again by trying to be who you were; you begin by honoring who you are now.

It’s easy to believe that time has passed you by, but love isn’t something reserved for the young or the flawless. It finds people who are awake to their own lives, who’ve lived enough to know what matters. You’re not late, you’re ready in a way you couldn’t have been before.

Start by reconnecting with yourself in the world: take classes, join groups that reflect your real interests, move in spaces where kindness and curiosity matter more than appearance. Online dating can be frustrating, but it’s also a tool; use it with clear boundaries and a strong sense of self.

You don’t need to prove your worth or hide your past. The right person won’t see your story as baggage, but as depth. Love begins again the moment you believe you’re still capable of being chosen, and of choosing well.

[Ask April Masini]

News Bulletin: Not every man is chasing after young or model-perfect women.

Three Names: Prince Charles. Princess Diana. Camilla Parker Bowles.

Hello.

Who got the Prince?

Exactly.

Please do not misunderstand. Our appearance matters — a lot. And, especially in dating.

Now, before offering any suggestions, I need to understand a few things about you, like….

1) Are you in a city or in a rural area? And what is the approximate population

2) What is the nearest major city? How far away is it from you?

3) You said you’re “not financially stable.” What does that mean? Are we talking debt? If so, how much?

4) What kind of work are you doing right now?

5) What does very well educated mean — and in what field? (There is a specific reason for this question)

6) You also mentioned being overweight. How many pounds are we talking about?

7) What’s your day-to-day like? Do you have hobbies that you actually do, or just ones you like the idea of doing?

8) Please give me a picture of what your day-to-day life looks like….. I want to understand what you are (or are not) doing to open yourself up to meeting new people, specifically men.

About this man from 20 years ago, why are you so sure you can’t reconnect with him?

You don’t need to guess if he’s married; find out.
Look him up online.
Confirm he actually is married. Don’t simply write him off.
Where does he live now?

We will craft our How To Re-Enter the Dating Scene Guide for Sunny together once you fill in some empty blanks for me…(And do a bit of research on our friend, Mr 4/5” Too Short, 20 Years Ago) …. 🌻💛

[Author]

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