Enlightening Answers: Staying Single and Positive and A Two-Timer

I am an attractive outgoing, positive 55-year-old woman and I have not been in a serious relationship for three years. I try all different types of things to meet new people. I go to singles events, I network, dance lessons, the gym, seminars etc. My question is how to stay positive and motivated when everything I do doesn’t seem to be working?

Trying Everything


Dear Trying,

Wow – you’re going for it. Good for you. The best way to stay positive is to love your life, which it sounds like you’re doing. I’d also focus on creating strong friendships. Studies show the best way for a woman to meet “that special someone” is through other women, because when we find a “live one” that isn’t right for us or that we can’t be with, we can’t wait to hook him up with a close friend. Also, having a fulfilling, rich personal life with friends fills your emotional needs, too. Dinner parties, brunches, birthday parties, holiday celebrations, etc. are more intimate opportunities to meet people than the kinds of events you listed. So stop worrying about what “isn’t working” and focus on filling your life with lots of other kinds of support. Good luck!


I met a man and he had just starting seeing someone else when I met him. He still sees her but we became close as friends and are attracted to each other. He always tells me he isn’t married and he only sees her once a month (he lives in Michigan, she’s in California) and that he can do what he wants. I treat him only as a friend but he’s always making suggestions in a sexual manner and I’m wondering what he’s doing and where this is going. I feel spiritually connected to him from all of our hours of talking and time together (we’ve never had sex). Now I don’t know where this is going if anywhere. What should I do? Go with the flow? Focus on him as a possible partner?

Flirting Friends


Dear Flirting,

Oh, dear. Do not pass go! Do not collect $200. Do not buy Boardwalk… Okay, sorry – that’s “Monopoly” speak for “stop!” This guy is a player. He’s not relationship material. He’s only looking for fun. If you’re having a friendship with him but waiting for him to realize he should be with you, then stop being friends. He wants to play with you, but he’s told you himself – he just wants to do whatever he wants. He’s in a long-distance, no-strings relationship because that’s all he wants right now. If you’ve spent “hours talking and time together” then he would know by now if he wants to see if there’s something between you or not. But do not “go with the flow” or “focus on him as a partner.” It sounds like you’re looking for a real relationship. I’d find someone who is, too. I’d go date other people immediately. You’re focusing your attentions on him for the potential, “it could happen” possibility you feel with him, not for what he’s actually giving you.

Good luck!

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