[samf]

Hi April;
I have been friends with a woman I work with for 10+ years.We are both now mid-fifties (but you’d not guess it). We are both married and having an affair is not in the picture. There are, however, signs of attraction and subtle flirtation. We chat frequently and laugh a lot. My problem is, I do not seem to know just where I stand with her now. About a year ago I began to notice her making frequent references to another guy who works with us. He is a friend of mine and the two of them chat fairly often. That was never an issue until these seemingly out of place references. Like, we would be talking about eating out & she would say, “Oh, Tom loves that restaurant” or “his favorite dish is” this or that. She would also refer to the two of them. It was like a woman talking about a new boyfriend she could not stop thinking about. It was pretty much confirmed when he walked into the room while she & I were having a typical pleasant conversation when she stopped and gazed at him dreamily for several seconds. (His back was turned). A few days later, the same thing happened, only this time it was for a full 8-10 seconds. I took it as if to say, “in case you missed it last time”. It worked. I would not make eye contact with her after that. The gazing stopped, but the frequent references in conversation did not. I am absolutely certain she does not have any romantic interest in this person. A week or so after this she offered another dreamy gaze, quite apparent for my benefit, at another guy, who I would bet my house she has even less interest in. Why would she do this? When just the two of us were conversing everything was great, but often if another guy came into the room she would make me feel invisible. My thought was that she is trying to tell me I am nothing special to her. But she almost always initiates our conversations, usually says things to keep me around when I do and, if anything, the subtle flirting increased a l bit. I don’t have a clue what she was trying to tell me. I finally asked her. Maybe a mistake, but I did not know what else to do. It did not go well. She got nervous, as did I. At first she dodged it and I let her off the hook. A while later I asked her again. She got very upset and basically said I was nuts. I am afraid that I came off too accusatory, when all I wanted was an explanation. My one wise move was not to argue with her about it. Things got pretty good again sooner than I expected. But sometimes she seems like she loves me and other times, it’s like, get lost. I’m sure I have my problems, I do tend to over analyze at times, but I am pretty affable. She is very charismatic, but rather narcissistic. That makes things a little tough, but I accept it as who she is and I believe she tries and does care. A few weeks ago I growled at her, for no apparent reason. Probably the first time. She has just started being friendly with me again. Did she over react? Do I? I want us to stay friends and continue to enjoy each others company. Any advice you can give would be greatly appreciated. This may not seem like it’s that important, but it’s dragging me down. What does she want me to think?

[Ask April Masini]

First of all, I don’t think you’re being honest with yourself. You don’t want to be just friends with her. 🙄 You want a romantic relationship with her. Besides, men and women can’t be friends. One person always wants more than friendship at some point, and sometimes both do — and this “friendship” just doesn’t have the honesty that a real friendship does. You’re not being honest with her now, and she isn’t being honest with you. When you asked her if she’s dating your friend it turned into drama because the two of you haven’t been honest with each other. So if you can accept that what you have isn’t a friendship, you’ll be able to move forward with a possible relationship. 😉

Next, you have to ask her out on a date! Invite her to dinner. Take her somewhere nice. And change the nature of the relationship from awkward to romantic. 😎 After ten years of not asking her out, I think it will be a relief to finally do so! I know you’re nervous, but if she agrees to go, you’ll get to know her romantically and you could have a lot of happiness. If she doesn’t, then you can put this decade of wonder to rest and move on. The worst thing that will happen if you don’t ask her out, is that you’ll live with the regret of not knowing what might have happened if you had. Regrets are the worst.

Let me know if you have any other questions — and let me know how things go — I hope you’ll ask her out this week!

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[samf]

I think you are right and I think I kind of knew that. Thanks for being direct. As for asking her out, not possible right now. It may sound like procrastination or excuses, but it’s not. True, I would be seriously nervous, but I would not be afraid to. So I do want to keep it platonic. I enjoy chatting and flirting. I think you are also right about honesty missing here. I am hung up on this “fake infatuation” she was displaying. I’d really like to know what that was all about. And, I seem to be a persona-non-grata at the present. At least this time I have some idea why.

[Ask April Masini]

I’m sorry that you won’t ask her out on a date. I hope you’ll consider playing the field and asking out other women who might be interesting. Since you’re in your 50s, it would be a real shame to lose out on dating opportunities simply because you’re nervous. 🙁 Most people are nervous when they ask someone out, because they don’t want to be rejected. I bet you have a lot of great qualities that the right woman will really appreciate — but if you don’t ask her out, she won’t get the chance (and neither will you!). 😉

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[samf]

I think we got a little off track. I am not looking for someone to date. Nor is she. She is married. I am married. I accept that it cannot be a romantic relationship. Maybe it’s not a true “friendship” but whatever it is, I’d like it to continue and keep it positive. I am quite sure she does as well, but she has me a little confused about that.

[Ask April Masini]

Got it. It sounds like you want me to help you understand your confusion. 😉 Let me know if I got that wrong.

The confusion comes from the fact that men and women can’t be friends — and you’re trying to bend that premise. That’s why you’re confused. The two of you are not friends — I’m going to guess that the two of you don’t go out on double dates with each others’ spouses. That’s what real friends would do. I think you’re looking for something that is more about just the two of you….. and since you don’t want to have an affair, I’m not sure what it is you want. And I’m pretty sure she doesn’t either.

In terms of her, it sounds like you don’t really know what’s going on in her marriage, but I can tell you that sometimes when things aren’t great in a marriage, people look outside their marriage to feel what they don’t get to feel inside them. That could account for her flirting with you, or you flirting with her — but rather than it going anywhere, there seems to have been a retreat away from the “third rail” which is an affair.

If you do continue this relationship with her, there is going to be confusion in it because it’s not friendship and it’s not dating — but men and women are always attracted to each other at some point, and that’s what’s happening here. The problem is, it’s not always attraction at the same time, and/or if it is, it sounds like the two of you are not both not ready to move forward beyond the flirting. So, confusion is the best you can get given these circumstances.

Let me know if I’ve missed something or if you have any other questions. And tell me how things are going.

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[samf]

Nope. You’ve got it. I am not very clear on what she wants either. I guess I was more concerned about that until now. It’s hard to say what I do want. I will try to nail that down. A little confusion does not bother me much. But, it seems like everything was pretty good until those head games. Not sure if that’s what they were, but it seemed like it. What would make her or someone act that way? Not sure what the message was. We seem to be having a little trouble communicating with each other.

[Ask April Masini]

It’s hard for me to give you advice when you don’t know what you want. The “head games” you’re talking about come from you both being married to other people, and flirting without making any intentions clear. 😕 She doesn’t know if you’re just being flirty or if you want an affair — and you don’t know either! 😉 When you know what you want, you won’t feel like there are head games or confusion, so much. 😉 If you have any other questions, I’m happy to answer them for you.

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[samf]

Actually, you have been extremely helpful. Your advice makes a lot more sense than anything I have been able to come up with. You have given me some valuable insights as to what might actually be going on here. In my brain as well as hers. Thanks so much for your help.

[Ask April Masini]

You’re very welcome. Feel free to let me know if you have any other questions. I’m here!

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[Ethan Morales]

The core issue here is clarity or rather, the lack of it. You and your coworker have a long-standing, playful, and flirty connection, but it’s layered on top of marriages on both sides. That means neither of you can fully explore romantic feelings without serious consequences. The flirting, dreamy gazes, and references to other men are all signals that she’s navigating attention, attraction, and boundaries in her own way. They’re not necessarily about you personally, but about her processing her own needs and perhaps testing emotional limits safely.

The confusion you feel comes from trying to apply a friendship framework to a dynamic that isn’t purely platonic. April is right men and women often struggle to maintain purely platonic relationships when attraction is involved. One or both people will inevitably want more at some point. You’re caught in that zone: you’re enjoying the flirtation, the connection, and the attention, but you’re also hoping for clarity about where you “stand.” That’s impossible to fully resolve without stepping outside the boundaries you’ve both set.

The “head games” or mixed signals are really a reflection of ambiguity. When she’s gazing at other men, it may be subconscious or a playful signal that she’s asserting independence, keeping attention fluid, or just exploring boundaries. It’s not necessarily about hurting you or making you feel invisible it’s about her managing her own feelings while maintaining decorum. Your reaction to it seeking explanations was natural, but it inadvertently put pressure on her, which created tension.

The pattern of initiation, flirtation, and then withdrawal is typical in situations where attraction exists but is constrained by external factors (marriage, work, social norms). Both of you are balancing the enjoyment of connection with the reality of commitment elsewhere. That push-pull is what’s creating your confusion, not malicious intent.

The healthiest way forward if you truly want to maintain this dynamic without overstepping boundaries is self-awareness and limits. Accept that you can’t have complete clarity, that some confusion is unavoidable, and that the relationship is defined by flirtation and camaraderie rather than romance or exclusive friendship. This means resisting the urge to demand explanations for every subtle gesture, focusing on the positive aspects of your connection, and keeping your expectations realistic.

Your curiosity about her motives and your own feelings is natural, but you have to recognize that this relationship exists in a gray area. It’s enjoyable but inherently unstable if you seek certainty or romantic escalation. Enjoy the banter and connection, but separate it from personal validation or emotional dependency. The “head games” are just a symptom of trying to balance attraction with reality and once you see them this way, it’s easier to stay sane and continue enjoying the friendship on its own terms.

[Sally]

You have been tangled in this push pull with her for so long that you are trying to decode every look, every comment, every shift in her voice. That kind of thing will wear a man out, especially when the friendship matters to you.

But here is what it really looks like from the outside: she loves the attention. She loves knowing you care. She loves the flirt, the chemistry, the spark. But the second she feels you getting too close to the truth, she panics and pushes you away. That is why she talked about other men right in front of you, she wanted to remind you she had power in the room. Not because she liked those guys. Because she liked the effect it had on you.

And when you finally asked her about it, she could not handle the mirror being held up. So she denied, flipped it on you, and made you feel “crazy.” That is what charismatic but insecure people do when they are caught in mixed signals.

You did not imagine any of this, you just cared more deeply than she was willing to admit.
If you want to keep the friendship, you are going to have to stop reading into her behavior and stop giving her that emotional space where she gets to play hot and cold. Keep things light. Keep it surface. Do not feed the flirt, and do not go cold either. Just steady yourself.

And remember: the woman who truly sees you does not make you feel invisible when someone else walks into the room. She keeps you right there beside her.

[Tara]

She’s not in love with you. That’s it. She’s not auditioning for an affair. She’s not secretly signaling some deep romantic code.
She’s feeding off the validation you give her — and then punishing you the second she feels you’re asking for clarity she has no intention of giving.

Every “dreamy gaze” she offered at other men wasn’t a romantic sign. It was a performance, and you were the audience. She wanted a reaction, and she got it. You felt insecure, invisible, confused. Exactly the kind of emotional ripple narcissistic personalities enjoy causing when they’re bored.

Then you asked her about it — and she flipped out not because you were wrong, but because you broke the unspoken rule:
You’re allowed to feel confused. You’re not allowed to confront her about why.

She wants control, not accountability.
And here’s your part in this mess:
You keep acting like a man waiting for her to reveal some grand emotional truth, when all she’s doing is juggling your attention like a toy. You’re married. She’s married. The line is firm. She knows it. You know it. But you still want her to declare you “special,” and she still wants the thrill of keeping you off-balance.

When she’s warm? She’s feeding.
When she’s cold? She’s reminding you it’s on her terms.
When she ignores you around other men? She’s managing the spotlight.

You growled at her? Yes, she overreacted. But she overreacted because any hint of you stepping out of the compliant, validation-provider role threatens the dynamic she built.
You didn’t growl because you’re angry at her.

You growled because you’re exhausted from playing a game she controls.

You want to stay friends? Then stop expecting emotional clarity from someone who thrives on being unpredictable. Keep it light, keep it surface, keep it professional. She will treat you well as long as you stop looking for meaning where there is none.

[Author]

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