Her Best Friend Used Her

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DEAR MIDLIFE BACHELOR:  I need some assurance basically. I took a stand in a relationship that felt right when I made it and for which my friends all applaud. However, I don’t take my friends’ applause too seriously as they are all married so it’s easy for them to look on and think they know what’s best.

Anyway, the guy in this case is/was a friend. I’ve known him for about a decade now. Three years ago we dated. I was his second girlfriend ever; he was 37 at the time I believe and I was 29. His first relationship lasted a couple months. We technically lasted 4.5 months; we randomly chose a beginning date; we had been spending a lot of time together for at least a month prior to that date. We were also each other’s first sexual partner. He wanted to wait until marriage, I didn’t see a problem with sex before marriage. It happened.



We broke up not long after we started having sex. I have since discovered the whole break up was a big misunderstanding … it was a communications mess. So, after some time apart from him and then some frustrating conversations, we decided to still be friends.

Our friendship after that was slow and awkward. I dated other guys; I know now he dated other women but the longest relationship he had was a month. I also know he has been sexually active in his relationships since me. Things gradually got better between us over a period of months until, for the last year, we ended up spending a ton of time together and talking to each other all the time.

We were both frustrated with the dating scene and sexually frustrated last summer so we had no-strings sex. We discussed it first and mutually agreed that if either of us were uncertain or wanted more than just sex that we would be up front with the other person. We were both seeing other people at the same time and if one thought they’d met someone they liked the other backed off.

He met someone at the end of summer and told me right away, I backed off completely. But then within a week he would tell me he didn’t see it lasting, that he would break up with her. He would chat with me in explicit ways so I’d think he was done with her but then he’d mention her and I’d have to ask if he was still with her to which he would reply yes. He was with her a total of 2 months. These were 2 very confusing months for me. I told him after the 1st month that I could not talk explicitly with him anymore and he agreed. He still stayed in touch though and we talked about regular stuff. Things shifted from a sexually based friendship to a regular friendship.

When he broke up with her he immediately made plans to see me. He was anxious to see me, which was awesome but then I began wondering if he was anxious because he wanted to pick up the sexual friendship again. I realized I couldn’t go back to that.

I told him that I didn’t want to continue our previous arrangement, I wanted more from him. In the end we decided to just be friends; we both expressed how great the friendship was and that we didn’t want to lose that. But, despite this, our times together always started out as platonic good fun with a friend and end with sex of some sort. So I backed off slowly at first and then, for the last month, completely backed off.

I didn’t initiate any contact with him but he pursued me to the point that I talked to him or saw him almost every night. Technically we were just friends, but it felt like a dating relationship. He was my date to my office Christmas party, he wanted to help me renovate my house (and was insistent on this point) and said he was always up for a road trip to another city to look for stuff for my renos. He would often say “we” can do x, y and z to my house, he’s usually very keen not to use that pronoun, even when we dated, so it seemed odd to me that he kinda took over my renos and stuff. I was very confused. The sexual part of our friendship had tamed down to some degree as I wasn’t as into it as before, but it was really hard to keep that out of the friendship and hard not to wonder if this was going anywhere.

Also, during this time (about 2 months) he was meeting other women but wasn’t up front about it. I would ask him generally how dating was going and he’d say “meh”, nothing great. I finally point blank asked him about one “friend” he had, who was it and if he was seeing her and he admitted he was but only to see if they were compatible. He said he had concerns about her. His concerns sounded very similar to the previous relationship. He insisted that our time together was valued and that I was more than an ego boost to him (I told him I couldn’t help but feel a bit used at times although I realized he wasn’t consciously using me).

So … I was tired of where things were at with him. He was one of my best friends and it was tough to think of losing him, but I couldn’t hang out with him one night and then wonder who it was he was with the night before. He was only mentioning other women as “friends”, he wouldn’t say their names so I would be left wondering who these friends were. He’s always had female friends but since we broke up and he started online dating he had gathered a large number of them who, to me, seemed sketchy. I hated how jealous I was so I called it quits. I told him I couldn’t handle the friendship anymore the way it was, that I wanted more but needed to move on if he doesn’t and the friendship was not allowing me to move on. I told him if he ever wanted to get together and stop dating other women to call. He expressed sadness at my decision but respected it.

Now … well, it’s been two weeks since I stepped up and broke all communication with him and I’m doubting. I don’t think he was using me, and I do think he cares about me. I have come to know him well and know that he takes a lot of time to decide big stuff and wonder if I had to take such a huge stand with him or not. I don’t miss the jealous feelings but suddenly I have a lot of time on my hands that he used to fill. I miss telling him certain things, laughing about stuff that he and I get. I lost my best friend and wonder if I was hasty. Maybe I could have salvaged more of the friendship than I did, but then remind myself that I tried for two months to salvage the friendship and it didn’t work. I’m not sure that a question is very clear from my ramble … perhaps it’s this:

If a guy hasn’t started dating and being sexually active until mid-life, is there a need to play the field before settling down with someone?

Oh, one more thing, since dating me he has been dating women who are his age or older (much older) which makes me think he is disregarding me because he thinks I am too young for him. Thanks for any insight you can bring.


Thanks for writing in. I don’t think it matters one bit whether someone waited until midlife to have sex … my answer would still be the same. Even though this guy was one of your best friends for a long time – he was absolutely USING YOU … and I think that is wrong wrong wrong. Now you allowed this to happen – so it is 50% your fault … so you cannot entirely blame him. He may not even consciously realize what he was doing … but he was definitely using you.

In my book, when you really care about someone – you won’t see other people at all. I, personally, would not feel right about sleeping with one woman while actively meeting women via an online dating service … you just don’t do that if you have any integrity at all. And since you two are such good friends, I think that makes what he did even worse!

I know you miss him a lot … there is a void, a vacancy in your life right now … but I think you did the absolute right thing by breaking it off with him. I would suggest zero contact with him in the future in all cases. I’d put him in your rear-view mirror, and never look back. If you don’t do that – you will never be able to find the right man who won’t do stuff like that to you. And the sooner you cut off communication with this guy, the sooner you’ll find Mr. Right. If you were to keep your friendship with this guy (even if platonic), then you’d be using up your personal bandwidth that you would be better off spending finding someone WORTHY of you – does that make sense?

Anyway – I applaud your recent decision, and support it completely. You did the right thing. Be strong. Hold the line. Don’t back down. Don’t answer his phone calls, nor his texts, nor his emails – as that would be wasted energy on your part.

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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.