How Do I Stop Leading People On?

Dear Dr. NerdLove,

This is a pretty minor problem compared to a lot of the ones that you deal with, but I’ve really valued your advice over the years, so I thought I’d send it in anyway.

I was very nervous and awkward as a teenager, but I have spent the last decade working actively on my social skills. I’m proud of how far I’ve come! I’ll always be a bit dorky, but I am able to have conversations with a wide range of people. I have an upbeat personality and really like getting to know people, but I am also a bit over accommodating.

This leads to a dating problem—I feel like I lead guys on. When I’m on a date I tend to smooth over any conversational rough spots, get enthusiastic about their interests, and actively listen to the things they want to rant about. If someone isn’t engaging with me and I have to carry the entire conversation, I can and will do that. I can tell that a lot of guys leave our dates feeling like they’ve really connected, only to be completely blindsided when I reject them. I feel like I’m the woman on the other side of every story about how “I thought it was going so well, I just don’t know what happened.” Rejection hurts, and it especially hurts when you didn’t see it coming. I’m sure all women experience this to some extent, but my I-Don’t-Want-To-Date-You conversations can get super messy and make me feel like the bad guy.

I’m not trying especially hard on dates and never promise anything–it’s my default conversational style that’s the issue. I really want people to have a good time, and don’t know how to do “lukewarm.” To a lesser extent this is also a problem in my friendships, as it’s become a pattern that other people get much more invested in me than I do in them. I think sometimes by trying to be nice in the short term I end up hurting people in the long term, and I feel awful about that.

Do you have any advice on dialing it back? Should I learn to let awkward silences hang and invest in a resting bitch face? I know that there’s got to be middle ground between “what I’m doing now” and “actively being mean” but for some reason I’m finding it hard to navigate. Or should I just accept that part of life is sometimes accidentally hurting the almost stranger that you are eating a giant plate of tacos with? I don’t want to close myself off to other people.

Thank you for your time!
Feeling Rotten About Unrequited Desires

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This is one of those weird times when I can understand what you’re going through, FRAUD, but man I can empathize with the folks you were on dates with. It can be really frustrating and confusing when it seems like you were really vibing with someone and having a great conversation only to find out that… well… they weren’t actually feeling it. Now you’re left wondering just what the hell happened, when all signs pointed to everybody having a great time.

But while I can see why there would be dudes who feel like you’re leading them on, the problem is, ultimately, one of discomfort in the short term.

You mention that this is an issue that you have with your friendships too, which I think is a bit of a clue as to where the problem lies. The fact that this tendency towards over-accommodation seeps into your entire social life suggests that you have issues with being a people-pleaser. On the surface, that’s the sort of thing that sounds like a non-problem; what’s wrong with wanting to make sure people are having a good time? Well, it comes down to the cost of paying so much attention to other people’s emotional states. One of the problems that people-pleasers have is that this desire to accommodate others’ needs comes at the expense of their own needs. Giving so much to others often means that either the people-pleaser is missing out or giving up resources that they might need, whether those are material resources or intangibles like time or emotional bandwidth. So someone may agree to take up responsibilities at work that tax their ability to get their own work done. Or they may agree to so many things that they don’t have time or energy for and run headlong into burn-out.

And of course, people-pleasers tend to be a magnet for toxic people who love to take advantage of them.

In your case, your behavior is giving the impression of being far more invested than you actually are, leading to lopsided — or non-existent — relationships. I have to imagine that there’s also a psychic cost to this as well; dealing with the constant mistaken impressions or imbalances in your friendships must get exhausting under the best of circumstances. And that’s before we get to the (understandable) guilt at feeling like you’ve lead people on.

I absolutely get why you feel like you need to carry the conversation. There’s a strong sociological aspect involved here; even in this day and age, women are socialized to prioritize the feelings and emotions of men over their own… even when that hurts them. And let’s be real: those awkward silences or the inability to keep the conversation can be uncomfortable, even anxiety-producing. So I get why you feel like you have a duty to carry on the conversation. But — as you’ve noticed — the end result is a problem of its own.

So my first suggestion is that you start to interrogate just why you feel the need to be the person who makes sure everyone has a good time, no matter what. Does this come from a sense of a lack of self-worth? Are you trying to prove your value or justify your presence in people’s lives by being a people-pleaser because you don’t feel like you have any value on your own? Do you feel like you need to take on the responsibility because someone told you this is what you need to do? Do you not feel like you have the right to just hang back and not carry the entire conversation on your own? Or is it just as simple as feeling like someone needs to do something about that uncomfortable moment and you just end up always being the one to step up?

The more you can understand just why you feel compelled to do this, the easier it will be to dial it all back.

Notice I say “dial it back”, not “be mean”. There’s a vast difference between the two. You don’t need to overcorrect from being too accommodating to being mean or contemptuous.

That’s why my second suggestion is to do less. I realize this seems like a duh-George answer, but I think if you look at your life, you’ll see many places where you go above and beyond the call of duty, to the point of absurdity. By choosing to do less — to embrace the concept of choosing not to fill the emptiness — you carve out more time and emotional bandwidth for yourself. So, rather than rushing to fill in the conversational gaps yourself or carrying the entire conversation on your own shoulders, simply… hold back. Let the silence or the awkwardness be, instead of trying to fix it. This has two benefits. First: it means that the other person is going to have to take responsibility for their end of things. Dates — and conversations, for that matter — are collaborative exercises. The whole point is for mutual engagement and mutual connection. When one person is doing all the work, it’s no longer a partnership. At best, it’s a lecture. At worst, one person is doing all the work and the other person is alternately reaping the reward or sitting there in increasing discomfort. That ends up being lose/lose for everyone. The second benefit is that it ensures a more genuine connection with the people you’re dating. One of the mistakes a lot of people make is that dating is supposed to be easy. If you’re struggling to connect with someone, for example, that’s often a sign that there’s a fundamental incompatibility at play. You may have incompatible interests or personalities. You may have a clash of values, or they may simply be uninterested. Forcing the issue by carrying the entire conversation on your own creates a false sense of connection because, well, one person’s trying to paper over that incompatibility by themselves.

(It’s worth noting: there’s a notable difference between an awkward but genuine connection and a lack of compatibility. It’s the emotional difference between trying to figure out what side of the USB plug faces up and using the wrong plug entirely.)

My third suggestion is that you get comfortable with discomfort. If you don’t fear an occasional awkward moment or lull in the conversation, you won’t feel the need to fix it. Every conversation has its peaks and valleys. Sometimes those moments where the conversation dies off aren’t signs of something being wrong; it’s just the natural rhythm of the interaction. If you can learn to be comfortable with momentary discomfort, you’re in a better position to tell the difference between companionable silence and signs that the two of you aren’t connecting. Plus: it means that you won’t be forcing yourself to prop up somebody’s entire emotional state on your own.

Don’t be afraid to prioritize your own comfort or your own lack of interest, especially on dates. You’re seeing if you and that person are a good match, not acting as a cruise director. Take a step back and let other people carry their end of the interaction. You’ll have much stronger connections with the people you do like, and you won’t end up accidentally leading on the people you don’t like.

Good luck.

***

Hi Doc,

I’ve thought about writing in before but I’ve never had enough real motivation until now. I’ll try to keep it brief.

Over the last 7 years (woof, that long already) I’ve developed a FWB situation with a woman I met in undergrad. We texted on and off for most of the first half of the decade until we lived closer to each other. Then we began hooking up in 2017-2018 until she called it off in fall of last year.

We’ve become pretty good friends over the course of us knowing each other, and I care deeply about her. However, she’s not really as invested, which is why she called it off , which is fine. That’s normal. Stuff like that ends. It’s just begun to feel unhealthy in the last year.

After she called it off, we agreed to give each other some space, but we keep coming back to text each other. Neither of us want to admit it, but she likes the attention I give her, and I like being in close contact with SOMEONE who cared enough to fuck me. I’ve tried to tell her that it’s often painful for me to continue talking to her because I’m not over her, but she won’t stop. And I give in every time because I’m craving SOME kind of intimacy (even if it’s just a ghost of it).

Is there a way I can break this off? I feel kind of used for attention. She’ll even sometimes send me music that she knows will turn me on. Like. In a flirty way. But sometimes she’ll shut me down if I try something similar. I can’t let her go and it’s starting to feel kind of co-dependent. What should I do?

One Sided Affair

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This one’s easy, OSA: boundaries, boundaries, boundaries. You need much stronger boundaries with your former FWB.

You’re 100% correct: she’s digging on the attention you give her. She may not be emotionally invested enough to keep up the benefits part of the relationship, but she’s clearly not willing to give up the charge of knowing that you still want her. That’s why she’s playing this game of “go away a little closer”; she’s giving you just enough of her attention to keep you hooked, but without ever actually paying off what she’s offering. That’s why she’s willing to flirt and flirt and tease and tease, right up until you start to make noises about taking this somewhere more interesting with accompanying squishy noises. She doesn’t want the affair, she just wants the knowledge that you want her, even though she doesn’t want you.

Quite frankly, it’s a power-trip for her. As long as you’re letting her get you wound up, she has power over you, power that she expresses by teasing you and then shutting you down. And, y’know, if you were into this sort of weird ass orgasm-denial play or you had consented to it when you ended your FWB relationship, that’d be one thing. But you aren’t, you didn’t, and this is actively hurting you and making it harder for you to get over her.

Similarly, it’d be one thing if she didn’t realize how much this was hurting you. But she does. You straight up told her. And she’s continuing to do it anyway.

That tells me pretty much everything I need to know about her. And it tells me what you need to do.

But you aren’t going to like it, my dude.

As much as I hate to say it, she didn’t just end the “with benefits” part of your relationship; she also ended the friendship. The way that she’s treating you is not how you treat a friend. She’s actively disrespecting your request that she stop teasing you and flirting with you because to do so would be inconvenient for her. It would deny her whatever thrill she’s getting from your continuing to be in her life and continuing to want her. It’s cruel and it’s unfair to you and if she actually cared about you, she’d goddamn listen when you said “stop“. But she didn’t.

Just because y’all had a casual relationship doesn’t give her the right to treat you casually.

The only way to break this off is to make a complete and clean break. First: tell her, straight up, that you’re ending things and why. You can’t have her in your life when she ignores your very reasonable requests to stop flirting with you. You especially can’t have her in your life when her behavior hurts you and makes it harder for you to get over her and your relationship together. Send her an email, a text, something, and them immediately take the Nuclear Option. That means blocking her on social media, blocking her number on your phone, deleting her Skype handle, taking her off your Venmo… every way she has of getting in contact with you or worming your way back into your life. And it needs to be immediately after you send that last email. You will feel as though you owe her the chance to explain or to make things right. You don’t, and she won’t. This will just give her the opportunity to do what she’s done over and over again: reel you back in. You already know that you have a hard time saying no to her, so don’t put yourself in the position of having to. She fucked around, and now it’s time for her to find out.

The thing to keep in mind: this isn’t about punishing her. This is about enforcing your boundaries. Boundaries are useless if you don’t actually enforce them. If you draw a line in the sand and don’t do anything when someone steps over it, all you’ve done is tell them that your requests are optional. Having strong boundaries means that there are consequences to actions, yours and theirs. In this case, the consequences of her actions mean that you cut her off. The consequences of you enforcing your boundaries means losing a friendship you’d rather not have to give up. But, unfortunately, she’s proven that she’s not worthy of being friends with you. She has given up that right through her actions, and it’s time for you to do what you need to do in order to protect yourself.

As a wise man once said: “I may love you, yeah, but I love me more.”

It’s time to love yourself enough to tell her to go away and make it stick.

It will suck now, but you’ll be better for it — both in the short term, as you get over her, and in the long term as you learn not to let someone treat you this way.

It’s a sucky situation, and I’m sorry that it’s come to this, OSA. But this is the best thing you can do for yourself.

Good luck.

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This post was previously published on Doctornerdlove.com.

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