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DEAR MIDLIFE BACHELOR: I have been dating my midlife bachelor for the last couple of years. We are close and

do most things together and work in the same field so there is very little time in our lives we do not share. He made it clear when we began dating that he has trust issues and I guess I did not suspect how deep-seated they were. He gets very upset if I do not call if I am running late, call him from the house phone when I get home, stand too close to other people, the whole jealous-insecure drama thing. To alleviate his concerns, I have taken him out several times to functions I attend, charity events, inform him of my whereabouts and who I am hanging out with. I have modified my schedule and have very limited time to myself so we can work on building his trust. I know it is a long road to hoe but he is worth it. However, here is the two-part clincher. He has several female friends that he maintains supposedly platonic relationships with. Nothing wrong with that. So here is Part One: They tease back and forth and call and email each other and sometimes that teasing becomes just ever so slightly inappropriate. I have brought


this to his attention and he has said, “There is nothing going on, they are long-time friends, we are just teasing each other and he has been a bachelor many years and that is just they way things are until we decide to get married.” He also keeps photos they have sent him of themselves beautifully ‘in flagrante’ (admittedly sent before we were dating) on the computer after I asked him to just save them elsewhere and take them off so I don’t have to see them.

Part Two: I think, “OK, I am reasonable. If I just know his friends like he knows mine all will be a little easier to manage.” So I ask him why we never go out with his friends and how come I never hear him talk to them when we are together hanging out at the house, we never go to their parties, etc. and that we should set up some dinners out to meet his friends. He then tells me after some evasive mumbling that, “Oh, I asked and they don’t want to meet you.” I pointed out that that seemed weird behavior and he just shrugged. He says he can’t force them to meet me, and that is true. He also insists that if I have him choose between his friends and me I will have to give up all my friends.

Am I on crack? I am a very logical common-sense person and this is just making me bananas. Is this bachelor behavior or just plain bad behavior? Any options? Suggestions? ANYTHING? I have looked all over and I think I am the only one with this bizarre issue. K

MLB ANSWER: Hi K – I can relate to the concept of having some very hot female friends who do things or act inappropriately at times with me … but I’m personally always careful to avoid any appearance of impropriety … which means especially in front of my girlfriend, I am cognizant of her feelings and keep all boundaries fairly well-defined with respect to my female friends. Those same female friends know that they need to accept my girlfriend and do things with us as a couple at least part of the time – and this strategy does seem to work out well for all parties … which means that my girlfriend does not get jealous, and my female friends don’t feel like I ignore them when I’m in a relationship. I extend the same courtesy toward my girlfriend that I expect her to extend toward me – concerning pretty much everything.

In your case, it sounds like your midlife bachelor boyfriend is looking at things strictly from his own point-of-view … and not necessarily considering your feelings. I mean – he has trust issues which you are expending energy working through with him (very nice of you, by the way). Now you would think that because he has trust issues – that he would be sensitive toward the appearance of anything inappropriate with his female friends … but that does not seem to be the case. In my mind, he is being a bit selfish … and it does not sound like he realizes it.

So what do I recommend you do? Well I can tell from your grammar that you are a very well-educated person … and so I assume that he is, too. My suggestion is that you in a very nice way remind him how you are working through his trust issues … and explain that trust is a two-way street … that your hope is that he can work toward being more aware of your feelings about his behavior toward his female friends. You cannot insist he abandon his female friends nor can you force those friends to embrace you … but you can simply ask that he take your feelings into account with respect to how he treats those female friends. Does that make sense? Tell him his karma is just slightly out of balance, and with some fine-tuning equilibrium can be achieved for all.

Oh – one more thing. You said his female friends sent him photos of themselves “in flagrante”? I admit I had no idea what that meant … and after a visit to and, can I please confirm that this means they sent photos of themselves essentially caught while having sex? Is that right? Wow – that is outstanding! Please forward these photos to me at once. ha ha I’ve had my own female friends send me some fairly inappropriate photos of themselves before – but nothing like that!

You might consider tossing this topic out on our Midlife Forum, too – just to get input from others.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.