Answers To Your Questions About Dating At 50+


When is it right to start dating?

Can you tell me when it is right to start dating after your spouse dies? I find it very hard to go out into the dating world and I am afraid to trust anyone. I hope this doesn’t sound dumb. — Pat D., 58, W. Keansburg, N.J.

Pat, Your question isn’t dumb, it’s extremely important. I’ve had so many widows and widowers ask the same question that I wrote an electronic book entitled, “After the Healing: A Guidebook for Widowers and Widowers.” You can read about it at The first question to answer is: “Have I properly healed?” If you feel you have, then you’ll be faced with the big challenges — where to go, what to do and whom to trust.

Status obsessed?

I am an intelligent, warm and fairly attractive middle-aged woman with a teenage child. I work two different jobs to provide for us. We don’t have much but we manage. I have noticed a disturbing reality when I date. Most of the men I have met seem to be more concerned with my financial status and career title than with who I am as a person and how well we do or don’t get along. Sometimes I have felt as if I’m being qualified rather than dated, and have come up short because I am not making a large salary. How can I sort out the people who will value me for me and not for my resume or financial statement? — Deanna D., 50, Horseheads, N.Y.

Deanna, I suggest you take the Loveawake Relationship Test to help you sort out your relationship needs and readiness. Let the professionals help you, that’s the business they’re in. More than anything else, by doing that, you’ll improve your chances to meet a man right for you.

Age appropriate?

Do you have to use a special personals site if you are over 50? I am 58 but pass for at least 10 years younger. Most personals sites seem to only attract men in their 30s and 40s, which is a waste of my time, as I have already raised three kids who are in their 30s. — Barbara R., 58, San Diego

Barbara, you should use a special personals site and it’s called Yahoo! Personals, the largest and most popular matching site available. However you must designate the age of the men in whom you are interested.

What if she checks my ID?

I started communicating with someone on the Internet and she makes my heart melt. She is 36 and I am 55 but she thinks I am 38. Even though I look 15 years younger I feel afraid to tell her the truth. We have plans to meet in the spring but I don’t feel comfortable meeting her unless I let her know my true age. We seem to care about each other greatly. What should I do? — William E., 55, Loch Haven, Penn.

William, you’re living in a dream world and being dishonest. You’re setting yourself up for a fall by masquerading as a 38-year-old. If you aren’t honest with her before flying to meet her, she will leave you stranded at the baggage claim area of the airport when she comes to pick you up. Not only will she be disappointed in how you look, she’ll also be angry that you were dishonest. You’ll have wasted your time and hers. Avoid all of that by being honest now. Perhaps you’ll lose her, perhaps not, but better to find it out now than later.

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Talk a little or talk a lot?

How does one know how much communication is appropriate for getting a relationship started? I find that some men will want to talk everyday and then there are others who seem to hardly want to communicate at all. It seems like the ones that I do not care about are the ones who keep on communicating after I stop and the ones that I do communicate with on a regular basis seem to come on strong and then stop communicating. They seem to be genuine and sincere during the conversations. Is this always so complicated? — Lynette E., 53, Des Moines, Iowa:

Lynette, older singles, especially men, are impatient. They want it all now. Getting to know someone shouldn’t be rushed. The reason you don’t care about the ones who overly communicate is they are coming on too strong and appear desperate. When a person has confidence, that person takes it slow and easy and that’s how you should take it. At 53, you’re young. There’s no reason to rush. If someone tries to rush you, that’s a sign that they’re needy.

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