Just the Tip: When a Work Fling Sours

just the tip work fling gone sour

Just the Tip logo with Jera BrownJust the Tip is a bi-weekly sex and relationship column from queer non-monogamous kinkster Jera Brown. Here you will find interviews with sexuality researchers and educators as well as smart and compassionate responses to anonymous questions. If you would like to be interviewed or have a sex or love question you’d like Jera to answer, email justthequestions@gmail.com or DM Jera on Twitter @rebellioustips.

So I decided to have a fling…yes, I am in a long-term relationship, but after many years I am going through a lot of questioning….most notably with sex…after years of trying different ways to be intimately attached to him through sex, it is very disconnected and feels routine, like with only him benefiting. Thus I decided to try something on the side.

Met a guy 12 years younger than me. Unfortunately at my job; don’t judge me…I don’t know how this works lol…in any event, he knew I was in a relationship. And he, supposedly, was single and dating.

So for about a month it was texting and “good morning beautiful” etc….great chats, etc….then we hooked up and did the deed. Now mind you, beforehand, there was the agreement that we were having fun and would be honest with each other in regards to how things would go. He said he didn’t want me to get “attached,” and I agreed, countering that he may be the one who might get attached. We agreed on being friends regardless.

Fast forward, we had sex, and it was great, but it seemed to end abruptly on his part, and he became very cold and distant right after sex. He then basically said he had to go to work. OK…

When he walked me to the car, he gave me a “side hug” and said, “until we meet again.” Then he just switched. No texting, no hello, nothing. Now though we work together, we rarely see each other on the job. Now it’s like he only responds to me when I text, and it is one-word answers. I have not pressured him on anything like a relationship or if he cares for me or anything. I just want a side piece, lbvs! 

But he shuts down if I ask if he was satisfied or anything, and the truth is, though it was good, I didn’t have an orgasm myself. I feel cheated and if I come at him, I think he takes it as attachment. Now I am beating myself up with regret that I was used or misled…worse that something is wrong with me or my vagina!

Any idea as to what I may have done or what he is thinking and if it is even worth this effort?

Side note, at work today, he gave me a side hug again. Makes me think we are good, but in any other communication I feel he has blocked me. 


Fear of intimacy, desire for intimacy he wasn’t sure you could provide. … There are so many reasons why he might’ve pulled away. The main thing is that you can’t put that on yourself.

One of the trickiest parts about intimacy is that somehow you have to be vulnerable enough to let others in and simultaneously strong enough that — whatever happens — you know that you are OK.

You asked if I had any idea what you might’ve done wrong. At this point, that shouldn’t be your main concern. Most of us beat ourselves up when romantic/sexual situations go wrong because we’re worried it means we’re not worthy. Until you accept that you’re worthy of hot sex and tender affection, any attempt to “be better” at dating will be a disguised attempt to make yourself more worthy.

Here’s my question: If he was only supposed to be a fling, why are you hung up over him?

What I’m really asking is: What did you need from him?

Until you accept that you’re worthy of hot sex and tender affection, any attempt to “be better” at dating will be a disguised attempt to make yourself more worthy.

The more you figure yourself out and what you need, the better your adventures will become. Because you’ll need less from your companions. You’ll be able to reap the benefits from great sex, wonderful companionship, and shrug off when things don’t work out, because … you’re still OK.

Regarding flings.

We like to believe that casual sex comes with no emotional attachment but, most of the time, that’s simply not true. And do you really want to separate out all the wonderful heart feels from physical intimacy?

Flings sound so simple in theory, because we think we can manage our expectations. But in practice, they bring out a whole mess of insecurities and desires that are beyond our immediate control.

Good encounters — whether they last a night or a decade — should leave you tender. Inside that tenderness can be so many things: gratitude, joy, luscious memories. But we can’t take the sweet without the bitter: residual longing, regret, fear. Hopefully the sweet outweighs the bitter.

You explained that you’re going through a lot of questioning around sex and that you’re in a relationship that’s not sexually satisfying. This means that sex is going to be sensitive and complicated for you — probably more so than you’d like it to be. Maybe you’ll be left more tender. Just be ready for it. When you understand that you let down your guard during physical intimacy, you won’t be so surprised when you’re overwhelmed with emotions.

Let the dude go because if he doesn’t want to keep seeing you, then he’s not worth pursuing. And know that his actions don’t reflect your worth or your dateability, and definitely not the quality of your vagina. Just keep exploring and don’t let anyone else decide how you feel about yourself.

One last thing. And with no judgement. Do you really want to attract men who are willing to be a part of an affair? And can you truly expect honesty in that situation? When you’re able to explore with complete honesty, it’s not that things might work out perfectly (because dating is often painful), but you will feel better about whatever happens. And figuring out how to be more honest in this journey will help you discover a more secure sense of self-worth as well.

Blessings on your journey.

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Jera Brown writes about being a kinky polyamorous Christian on her blog scarletchurch.com and a sex and relationship advice column, Just the Tip, for Rebellious Magazine. Follow her @thejerabrown.