I’m a fairly cute, extremely friendly woman who enjoys the energy exchange of a good flirtation. This has really pissed off a few guys. Truth be told, it’s ruined more than one otherwise decent relationship. The thing is, I don’t really think it’s wrong. I mean, flirting is one thing. It’s not like I’d ever do anything with the people I talk to. I know where the line is, and how to back away before things go too far. It doesn’t matter though. Most guys I’ve dated really hate it. What am I doing wrong? Am I doomed to give up flirting if I want to be in a relationship? Is flirting actually cheating? I’m so confused.

Fretful Flirt

Dear Fretful,

When I read your question, I had an immediate answer jump to my fingertips which is kind of weird for me. Often, I’ll read a question several times and carefully consider the answers. But this one came to me so fast that I thought maybe I was being rash. Before sitting down to write, I decided to take the question to a diverse group of friends and see what they thought. Here are their answers:

Friend 1: Hmm. Playful banter is fine with me. Touchy playful banter would get a side eye from me. Texting and the like would not go over well.

Friend 2: Playful banter in public, like in front of other people. No texting, no touching, though. That would be too far.

Friend 3: In our relationship, it’s shit going on without us meeting the other person. If I meet someone and give a thumbs up, she can do whatever she would like. Anytime someone feels the need to cover something up or lie, it is over the line.

Friend 4: Anything you wouldn’t tell your partner is crossing the line. No exceptions.

Four different people, four very different answers. But taken together, they support that gut reaction I had when I first read your question. Even though my friends have wildly different opinions, and despite the fact that they are all passionate about their responses, all of their answers are correct.

Everyone needs to discuss this in the early days of dating. What are your expectations? How about your partner’s? If flirting is important to you, be honest about that early on. You shouldn’t have to give up a piece of your personality for someone else. If you’re dating someone who isn’t cool with it, they are probably not a good match for you. And try as you might, this kind of outgoing personality trait is hard to stamp out completely. It can definitely be suppressed for a while (even a long while), but eventually one of two things is likely to happen. Either your inner flirt will bust out and make trouble for you, or you will become resentful that you can’t be yourself.

There isn’t a single definition of cheating that works for all relationships, with one caveat. Violating the boundaries that you and your partner have agreed on is cheating. Whether you agree to no texting, no touching, no kissing or no secrets—once you’ve set a rule for yourselves, it’s your responsibility to follow it. It’s okay, even preferable, to revisit your boundaries every so often. People change, and relationships change. If both people decide that something isn’t working anymore, it’s okay to throw it out and start over. The most important things are to find the structure that respects both of you and to keep talking about it over time.

Curious about cunnilingus? Anxious about anal? Do you have questions about queefs or problems with your prostate? Lucky Tomaszek is the education coordinator at >The Tool Shed: An Erotic Boutique, Milwaukee’s only mission-driven, education-focused sex toy store. Send her an email at [email protected] and she’ll get back to you with an answer.

About The Author

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Lucky Tomaszek, LM, CPM, is the education coordinator at The Tool Shed: An Erotic Boutique, Milwaukee's only mission-driven, education-focused sex toy store. Most mornings you can find her balancing her cat and her keyboard in her lap, working to make the world a smarter, safer place for people of all genders and orientations.