Dating at 50+ : Answers To Your Questions


Am I wasting my time?

I’ve been a widow for four years. I began to date a widower (wife deceased nine months). I felt it was too soon for him. We dated for four months. He went on a two-month vacation — to run away from me. Now we are dating again. I care for him very much and he cares for me. He informed me that he is confused. He did not think he would meet someone and care for someone again. Do you think I’m wasting my time and emotions on this man? — Gloria B., 56, Mission Viejo, Calif.

Gloria, dating a widower is risky business. Be very careful with your heart. He simply isn’t ready. So many widows and widowers have to deal with this very issue. The first three chapters are devoted to how soon widows and widowers should date again. By telling you he’s “confused,” he’s really saying he’s not ready to get involved again and may never be. If you try too hard, you’ll drive him away. I’m not saying it won’t work, just be very careful. Proceed cautiously and remember to protect your heart.

Race or drop out?

I met a wonderful lady online last November. After a whirlwind four months of really getting to know each other and discovering the depth of our mutual attraction, emotionally and physically, she slowed down and eventually disclosed her desire that I be slim like her, not rounded like me. She has decided to date others. So have I, though we continue to see each other periodically. When a guy slips from first place in the race for the love of a gal and finds himself competing with her new finds, should he give up or take the suggested step and try to regain first place? — Jerry E., 60, Fullerton, Calif.

Jerry, try to regain first place. Here’s how: You need to focus on you. I would start an exercise program and work hard on getting into shape and losing some of that “roundness.” This may not help your situation with her, but it’s going to make you feel better, live longer and improve your chances of meeting someone in the future. The next time you see her, thank her for inspiring you to change your life. Don’t delay another day. This adversity of losing her will likely yield opportunity in the future.

Wait or date?

I am recently separated after 13 years of marriage. Even though we didn’t have an intimate relationship for the last few years, I remained faithful. Should I wait a certain length of time before dating? — Charlotte D., 56, Camp Springs, Md.

Charlotte, should you wait to date? Why? It seems you already waited. If you weren’t intimate for a few years, you didn’t have much of a marriage. Get on with your life.

New reality

I have been a widow for two years. I have dated some but have found it hard to figure out the dating scene after being with the same man for 35 years (since my 20s). Things have changed so much. Expectations are different and so are relationships. Most men I have met are divorced at least once and have a very different perspective on things than I do. Should I adapt to the new reality or are there other people who value relationships as I do? — Pam H., 57, Limington, Maine

Pam, yes, you need to adapt to the new reality. You need to become dating savvy.

What’s the attraction of abuse?

Why do women stick to an abusive man who uses them and treats them like dirt? These women keep going back for more abuse! I’m a nice guy who treats women with respect. I’m loyal and devoted to them. Then they turn and dump me for guys who abuse them. After awhile, they call and ask me to take them back! I say “no” because they had it good with me and I refuse to let them hurt me again! If you do it once, you’ll do it again! Am I being unreasonable? — Richard T., 64, Pasadena, Md.

Richard, you say “these women,” which means more than one. If you’re only dating women who have been or are being abused, you’re finding women in all the wrong places. You should select women to date who have experienced healthy relationships and want healthy relationships. For the most part, women want and appreciate nice guys who treat them with respect and are loyal and devoted. Perhaps you’re trying a little too hard and coming off as too nice and too dedicated. Women may feel that you cater to them too much and that you’re too wimpy. So, evaluate the way you treat women and how they treat you. What you give, you should get back in return. That’s called balance in a relationship. Be nice but not too nice.

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Alex Wise served over 5 years as relationship expert helping women from around the world figure out the men in their love lives from an honest, male perspective. Alex is one of the contributors and editors for dating website. He is passionate about thought leadership writing, and regularly contributes to various career, social media, public relations, branding, and online dating communities.