Cannot Get into Platonic Room-mate’s Pants

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DEAR MIDLIFE BACHELOR: I have female platonic roommate that is very good looking. At first, I tried everything I could do to get her in the sack. Excuse my bluntness – she maintains that she wants to keep it at ‘just friends’. We are near the same age, 49, 50, I’m no ugly duckling, and a lot of my friends tell me to kick her out. I guess I have some far fetched dream that we would end up together one day. Anyways, she has been staying with me for eight months now and I’m not sure how to handle the situation. As long as she is here, it puts a damper on me “getting some” or just having a casual date over. We have been friends for over five years, so I would have a hard time giving her the boot. Any suggestions that you care to share would be worth their weight in gold. JJ

MIDLIFE BACHELOR ANSWER:   Thanks for writing in, JJ. I’ll be honest with you – even though our motto here at is “always go for it”, I think based on what you state that your chances of successfully scoring with your room-mate are extremely slim. I say this because it has been my experience that the older women become, the easier they are to get into the sack. And if she has resisted you for this long, then it seems obvious to me that she really does simply want to remain friends with you. And that’s not a bad thing – good friends and friendships are extremely important … especially in today’s world when so many people are losing so much out in the economy, etc.

Now you could continue to press this woman (your room-mate) but I don’t think it will work … more likely it will simply


increasingly annoy her. Maybe it is the challenge that appeals to you? I’ve been in situations like that myself in the past – and I found that after reaching the desired goal, it somehow wasn’t as great as I’d envisioned … sometimes the expectations exceed reality, if that makes sense. A better way to think of this is – how can you best expend your energy?   I’d say that chasing a new woman who is visibly interested in you would be a much better choice.

Another way that you could think about this is – what if the situation was reversed? What if you had a room-mate who was very attracted to you, and who you wanted nothing to do with? Would it not get annoying fast if she kept pressing you for sex? You’d likely start to avoid her, etc.

And yes – you probably do need to change your living arrangements … but I’d suggest doing your best to preserve your friendship with your room-mate because that friendship is obviously important to you. Just tell her that you feel like you simply want to live alone … and that it is nothing personal, but she needs to find different accommodations, and give her a deadline of say, six weeks. Good luck, JJ. You need to join our Midlife Forum here, and share some of your experiences. Let me know how things work out, okay?

UPDATE – I just tossed this issue out to our Midlife Forum, here is the discussion thread link

July 30, 2009 UPDATE – JJ wrote in with the following update, “She moved out and decided not to keep our friendship, which saddened me deeply. She was the love of a lifetime, and didn’t want a lifetime of love. I will miss her.”

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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.