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Bear Abby

From ugly dilemmas to sublime annoyances; Bear Abby has advice for all!


do i listen to my heart or head?

Tuesday, July 22, 2014

Bear Abby,

my boyfriend of 4 years left me in february, with a text message. he had no contact with me for 3 months. then called out of the blue, it was not a nice phone call on both parts. he called a few weeks later, and we had a nice talk. i understand why he left. there is a big age difference, i am 60 he is 25. he was not out at the time we were together. he has now come out of the closet and wants to live on his own.

we talked a few more times and have started dating. everyone tells me i am out of my mind for even seeing him. but in my heart i still love him and always will.

he is seeing me and another man, closer to his age (actually younger).

should i see other people or listen to my heart and stay faithful to him?

thanks for your input,



Dear confused,

In this case what you want and what he wants are very different. You want a life partner. He wants emotional security AND freedom. I do not believe those two things are compatible in the long run. If you want to keep seeing this person you should assume that it will not be permanent. If you are OK with that then no problem. If you want lifetime commitment you should probably look elsewhere.



I share the quandry

Sunday, June 08, 2014

Bear Abby,

i just read the letter about the Vegas Conference and i thought the writer had read my diary. I share both his excitement and panic about attending my first gay event. I am not out, but I have a great deal of freedom. I am older and certainly not inexperienced but I am just beginning to think in terms of relationship not just sex. I think I have finally worked up the courage to wear a skimpy swimsuit (i bought it anyway.) I have decided to hold my head up high and approach the opportunity to meet so many chasers with confidence and good humor. My fear is that i will chicken out once I get there and retreat from any party atmosphere or do something inappropriate. I have been contacted by several sweet men and am looking forward to meeting them. Do you have any advice (clothing, aggressiveness, flirting, non-verbal signals, etc) to prepare me for such a large group? I'm not looking for numbers or Mr Perfect, but I need to feel desired, not rejected.

-Virginal widower


Dear Virginal widower,

The main thing is to just relax and put yourself out there. You cannot meet people if you hide yourself in your hotel room. In terms of clothing I suggest the most physically comfortable and informal clothing possible. You will probably be spending the days hanging around the hotel pool and your evenings in the hospitality suite socializing. You will find that there will be a lot more chubs than chasers and you will also find that at least half of the attendees are physically larger than you are. Many guys find this to be liberating to not be the largest guy in the room. Do NOT be shy. Many chubs at these events tend wait for the chasers to make the first move. This approach could cause you to miss out on a connection with someone. Keep in mind the Vegas slogan of "what happens in Vegas stays in Vegas" and go for it.



When neither caution nor spontaneity is working for me

Saturday, May 31, 2014

Bear Abby,

I’m wondering whether I am just too smart for my own good, and that the lack of spontaneity I have in the process of dating is not costing me certain opportunities.

I am 62 and feel that my days of hookups have long since passed. I can’t really compete on the “market,” don’t respond well to flattery, but to be honest have been looking for a relationship that lasts for more than a night. I thought that by having a well-defined profile on sites, there would be less of a chance that I meet Mr. Wrong. I get encouraging words from nice men who have partners and are perfectly content in their relationships! Sorry, but I don’t think this is helpful!

I’ve insisted that I “get to know” someone with potential because of the number of times I’ve been hurt. Recently I decided to throw caution to the wind, and drove a short distance to meet someone my age with similar likes and experience with whom I had only talked on line for about a week. When I walked through the door, the disappointment on his face was evident. I know that chemistry is an individual and tricky thing, but despite our similarities, he didn’t even want to be friends.

The last time I had sex, I drove over two and a half hours across the state. We had talked and flirted on line for about two months, and I hoped that there was a connection that could flourish. We had fun and talked easily, but I thought it strange that he wouldn’t let me spend the night. When I sent a “thank you” e-mail, he responded by



Dear Dismayed,

Unfortunately your post was truncated due to space limitations so it ends with "responded by" so I may be responding to incomplete information.

I disagree that you are too old for hookups. Looking at your photos I think you are quite handsome and I believe that should you decide to be open to hookups they would happen. Most men whether gay or straight are motivated by physical attraction and a desire for multiple casual partners to a much greater degree than they themselves are aware of. Unfortunately male lust is also fleeting. Put two men together and this tendency for moving from one hookup to the next is magnified.

I'm going to give you the same advice I give to everyone who comes to me with laments similar to yours. Change your expectations. Stop husband hunting and start dating. Husband hunting sets you up for disappointment. Go out on as MANY dates as you can reasonably fit into your life. With each date set your expectation level to nothing more than having ONE pleasant evening. If there is mutual interest in sex, do it. If not then don't.

If you do this frequently enough then chances are that eventually you will "click" with one of them. When this happens it will feel like Mr. Right just fell out of the sky and into your life. It's like the old song by Diana Ross and the Supremes. You can't hurry love or if you prefer an older metaphor "you have to kiss a LOT of frogs to find a prince".

This column is for entertainment purposes only, and should only be used in that context. The advice presented here is only the opinion of the author and should not be construed as professional or expert advice. The owners of this site and authors are not responsible for the decisions you make in your own life including those based on any advice presented on this site.
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