Tall Woman Wants to Cross the Friendship Line

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DEAR MIDLIFE BACHELOR: My problem seems to deal with a few things such as a midlife crisis man, commitment phobia, and not wanting to risk ruining a great friendship. My male friend and I have been friends for years but we seem to keep coming back into each others personal lives. In 1998, when we both divorced our spouses – we hung out for a while, then again in 2002/2003 when I was in a crisis with my (off and on) man. Then this 3rd time, my friend and I have been “running around” together almost 2 years. The sexual energy between us is driving me nuts!!! But he’s so scared of getting involved, he runs away when things get close to being steamy. We’ve had a few kissing sessions, but no farther.

I understand his reasons for being afraid as all of the women in his life have left him and cheated on him and it’s made him very insecure. We are very close, and some who see us together say that “it’s good to see a couple so in love”. We just laugh! Others have seen us sitting in a bar and we told them that we are “just friends” but they say, “well, you can’t slip a piece of paper between you two” and it’s true!!! BUT,


as I told my pal, we seem to be having an emotional affair but not a physical one. I know he has feelings for me as I do him but he doesn’t want to act on them. I probably have more feelings for him than he does for me – but I’m the type that really wants the man to make the move. I don’t want to make the move on my pal as I want to keep his trust and respect. He says I’m getting too close to him and getting to know him too well and it scares the hell out of him. I take that as a compliment as he’s a very private person and a loner but it’s frustrating too!!! It’s like we are “excited as hell and scared to death” at the same time around each other. We have so much fun together and spend a lot of time together on the weekends, our cheeks hurt from laughing by the time Monday comes around. I even stay at his house if we’ve drank too much, but nothing happens.

When his friends find out that we are not dating, some of them have asked me out. He seems jealous then as they are more assertive than he can be. He’s told me that he doesn’t want me to go out with any of his friends!! Yes, I did get mad and go out with one of them, and he found out by the way the guy was acting guilty around him. It’s like he doesn’t want me but he doesn’t want anyone else to have me either. I told him that he’s emotionally unavailable, and I’m ready to date again (not marry, not move-in, but DATE). It’s been over 2 yrs since my husband walked out on me for a younger woman (23 yrs younger).

The really sad part about our situation is that I’m not sure if he’ll ever be ready for any type of relationship with me, or if it’s just that I’m taller than he is (3 inches) and he can’t handle that or the gossip. By the way, we work in the same building (over 1000 people) too, but not on the same floors and we don’t see/talk to each other much at work. We keep our work and personal life separate but sometimes I feel like “the dirty little secret” since he won’t officially date me. I feel like I’m back in high school again in good and bad ways. I feel young and free and happy around him as he has a sharp wit and great sense of humor. But I think he cares too much what other people would think of us dating (the odd couple).

I’ve went on dates with 3 other guys in the last year, but he’s the only one that I want to be with. He’s 8 yrs older than me which is why I think he’s also going through a midlife crisis. He worries so much about looking old and losing his hair that he can’t understand my attraction to him. We call each other our “comfort zones” and we feel like “home” when we are together. I let him have all the control over when we see each other: I don’t call him, I let him call me, etc. He also enjoys being single so he can “eye” the young girls. I say nothing about that because we are not an item, but it feels like we’re dating as we’re always together!!! He hasn’t been in a relationship for many years since his ex broke his heart. “Once bitten, twice shy, BULL, forever shy with him”. We get along great and are very close but I want more. Is that too much to expect after all this time? I’ve been patient and kind and he says that I know him better than his own family or other women have ever known him. Am I a fool, or is he worth waiting for?? I’ve tried many different things such as not showing up at our usual place and waiting to see if he calls me, and he always does! His fear of being hurt again is keeping him from moving on with his life. I’ve told him that he’s just made the wrong choices with his previous women. I just don’t know what to do about this man, but I’m crazy about him. What do you think I should do?

MIDLIFE BACHELOR ANSWER: If you’ve read much of this site, then you will know that the motto here is ALWAYS GO FOR IT … so if there is any doubt about what anyone should do in any given situation, then simply refer to that rule. And that is exactly what I suggest that you do right now. The worst he can say is “no”, and perhaps for whatever reason he is simply gun shy about dating, in general, or you, in particular. If you do not try making a good move on him right now, then you may find yourself waiting FOREVER for him … and in the interest of living a full and fulfilled life, I think you owe it to yourself to give him one more shot, else you should move on to greener pastures with respect to a lover.

Now I understand that he is essentially your best friend – and I don’t think you should jeopardize that. Good friendships are rare, and extreme valuable. So don’t go psycho on him if he rejects you – even if he doesn’t tell you why … he doesn’t have to tell you why, as the reasons are his own. If he does reject you, simply apologize for making your move – and then tell him it will NEVER happen again … and explain how important your friendship is to him. And leave it at that. I’d suggest NOT dating his friends – as that will serve no good purpose for anyone.

Let me try to add some of my own perspective here concerning the concept of dating your FRIENDS of the opposite sex. I have a handful of chick friends who have been my best friends for many years. Some of these women are knockouts, and some are not. I would not date ANY of them precisely because I value my friendships with them so much … which means if a relationship did not work out, then I’m sure the friendship would go out the window, too. And I value their friendships way too much to risk them. Better to fish off a different pier. Besides – these female friends of mine can offer extremely good insight and advice to me about women, and about me, etc. … which is another reason why I would not date any of them. Of course, I live with my current girlfriend – so for me, I’m not out looking for someone new right now.

The fact that you are three inches taller than him could be an issue in his mind. Yes – you would look a bit odd as a couple walking around anywhere. I hope you do not wear high heels. I once dated a fiery redhead who was four inches or so taller than me. She was from Pittsburg, and in the month or so that I dated her, I learned that she actually had a fairly mean disposition. She was very friendly in bed with me – but showed increasing signs of hostility and of having a chip on her shoulder towards men. After I found out that she liked to throw things when she was angry, I ended the relationship – but I did so over the phone! That’s the only time I ever did something so rude as a phone breakup – and I did so for my own personal protection! Anyway – my point is that he might view your height as exclusionary … and if that is the case, then do your best to put your amorous feelings aside, and just be friends with the guy.

One other thing I might mention or suggest to you (or anyone who is single at midlife) – give yourself a tune-up … perform a sanity check on your attitude, and also on your appearance. And come up with a deliberate strategy toward dating. There are some good sections to read in the Midlife Dating Advice part of this website. Of course, they are written for a man from a man’s point-of-view – but you can adapt them suitably for a female:

Midlife Bachelor Personal Makeover


Develop a Strategy for Midlife Bachelor Success

Good luck – please let me know how this turns out. And check out our Midlife Forum – where issues just like this one are discussed … and where you can get the opinions of other men and women.


Use our commenting feature below to share your opinion on this question or answer, or to offer your own answer, or you can always choose to discuss this in the Midlife Forum …
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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.