Dear Dana: Every Guy I Date Leaves Me To Get Serious With Someone Else

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana,

I have been single for three years, and I’ve found myself in a pattern I need to break. The last few times I’ve started seeing someone, we’ll be casually dating, having a good time, I’m thinking we’re headed in the same direction and then suddenly they tell me they are getting serious with someone else. This would be fine, except it always comes as a total surprise to me and has happened after six months—when I’m still working up the courage to ask where we’re headed!

I take equal responsibility in this: I’ve been cheated on by every boyfriend I’ve ever had, I’m still carrying those scars, and I am very guarded about my emotions and also wary about starting a new relationship. I need time to get to know someone before I feel comfortable talking about my feelings. To be honest even when I do really know people, I find it excruciating to talk about my feelings, especially if I know that the conversation might end in rejection.

The other thing that upsets me is without exception, these guys always contact me later wanting to have sex again, whether still with this new girlfriend or not. This leads me to believe that I must really be giving out the wrong signals (and that these guys are obviously jerks). You’ve chosen someone else over me, you’ve hurt me, and yet you think it’s totally cool to contact me for casual sex again? While knowing these guys are fuckboys, I do take some responsibility: I can’t stand for people to know they’ve hurt me, as I don’t want them to have any power over me, so I’m sure in some instances, they don’t think I care that much, so they assume I’m OK with this casual contact.

So I’m keen to break this pattern, but I have no idea how or when to ask someone where they see things going and to discuss what my boundaries are while we are casual (mutual respect, honesty, my time is just as valuable as yours, etc). I don’t want to bring things up too early and freak people out, or give them the idea I definitely want to get serious. But, equally, I don’t want to be ambushed after months of hanging out with someone.

I know that in order for people to treat me better I need to get better at talking about my needs and wants, but I honestly have no idea where to start and my self-esteem is non-existent right now. Please help!




Dear Buttoned-Up,

I once loved a man for an entire year before I told him so. I was so in love but I was so cautious, and protective, and wanted to make sure that he really, really felt the same way. I decided that the best way to make sure that he felt the same way was to make sure that he said “I love you” first. It now seems childish and petty, but at the time I was unwavering in my decision to not let him know how I felt.

What was extra ridiculous was that “I love you” was tumbling out of me most of the time. I was saying it to everyone who wasn’t him: plants, dogs I passed on the street, a room he had just left. I wouldn’t let myself say it to him so I whispered it to the universe whenever he wasn’t around.  But I couldn’t stand the idea that, if I said it first, he would only say it back out of obligation. I wanted to know, really know, that he loved me before I told him.

On our one year anniversary we were lying in bed and he finally told me he loved me and it released us both. I basically screamed back that I loved him too and then we held each other and giggled like idiots because we were finally free. The next day I was euphoric, smiling like a goon, barely able to contain my joy. Now, did he end up breaking my heart? Of course he did. Did I end up breaking his heart? Surely. Are two broken hearts the most typical result of most relationships? Yep.

You are afraid—afraid of being hurt again, afraid of giving away a piece of yourself to someone who won’t appreciate it, afraid of feeling weak and small and unwanted. You aren’t comfortable with feelings so you pursue men who won’t make you talk about your feelings, but when you do a Venn Diagram with “dudes who don’t want to know how you feel,” and “fuckboys” it’s just a damn circle. These men ask nothing of you emotionally because they don’t want anything from you emotionally. You’re getting exactly what you’re setting out to get and it’s driving you nuts.

Here is something that you already know: Six months is waaaay too long to wait to have the “where are we going?” conversation. If it’s month six and you haven’t already established were the relationship is going, it’s because your relationship is going nowhere. You say that you have to muster courage to have a conversation about a relationship, but I want you to really examine that thought. Why does it take courage? What’s at stake? What, exactly, is the risk? If you tell a man that you want to date him exclusively and he doesn’t feel the same way, what happens next? Does the sky fall? Does the world burn? Does your rent go up?

Back up. Sit down. Look at this from the long view: What an individual man thinks of you has fuck all to do with your worth as a human. Nothing. Maybe he doesn’t want to date you because he’s still in love with his ex-girlfriend, or he hates sharing a bed, or he’s afraid of feelings, or he doesn’t know what he wants for breakfast let alone for the rest of his life, or because he’s moving in two months, or because he doesn’t like the way you wear your hair. The point is that you really don’t want anyone who doesn’t want you. The idea of being rejected is so scary, but the real life experience of being rejected is less so. You say, “I want to date just you,” he says, “I want to keep seeing other people,” and then you figure out that he’s not for you and you never really liked him anyway and you move on and spend your time on more worthy pursuits.

The truth is when a man falls in love, he falls hard. Head over heels. It is obvious to you and him and your cat and everyone who walks by him on the street. It is obvious to the point that you feel bad for him because it’s slightly embarrassing, how much he likes you. When people go for each other they GO FOR IT and the conversation can become like an afterthought. If you’re dating someone and he isn’t making time for you, he isn’t checking in on you, he isn’t slightly obsessed with you, then you can relax and casually date him but know that this guy is fun but he isn’t your man.

I’m so sorry that those scummy dudes cheated on you. Please know that their actions had absolutely nothing to do with you—your value, your beauty, your intelligence, your worth. I mean, you wrote the sentence, “While knowing these guys are fuckboys, I do take some responsibility,” which right there shows that you are DELIGHTFUL. You know the guys who cheat on you? The type of guy who cheats on you? Stop dating that guy. The pattern here is you: You’re trying so hard to be cool and detached that you’re only responding to men who are also cool and detached and low-key awful.

Here’s my idea on how to handle the offers of sex post-relationship: Make a new contact entry in your phone called “NO.” Input the number of every dude who you no longer want to bang. Now, erase the contact that lists his actual name. And now, when you get a random offer for post-relationship sex, you won’t even know who is doing it, just that you once decided that he was no longer worth your time.

Fuckboys have a sense for these things. A dude I was casually seeing who stood me up and then never called me again texted me for a hookup on Christmas Eve while I was staying at the house of my then-brand-new-boyfriends’ parents. It’s like he could tell that I was happy and was like, “Oh hey can this dick show up and ruin your shit again plz?”

The question you need to ponder is less “how do I get a man to like me?” and more “how do I determine if a man is worthy of me liking him?” Relationships aren’t gifts that men bestow upon women. Relationships are agreements entered into by two people who find that they simply must be together.

Here’s another question: How’s it going? Is your staying super protected and not getting hurt plan working out? Not at all? Because the problem isn’t getting hurt. The problem is the fear of getting hurt. You said it yourself, you find it hard to talk about your feelings “especially if I know that the conversation might end in rejection.” But every single thing you do might end in rejection. Nothing is 100% perfect bulletproof guaranteed success. You gotta leap. You can leap with a guy who’s a safe bet or a guy who’s a risky bet, but you can’t escape the fact that both are bets.

The shit is self-fulfilling—you’re afraid of being hurt so you only roll with dudes who don’t ask you to open up emotionally who are also dudes who don’t care about your feelings who are also dudes who hurt you so you’re more afraid of being hurt so you only roll with dudes who don’t ask you to open up emotionally, etc. You know what you do once you’re hurt? You take care of yourself. You realize that guy was the worst and you pick yourself up and try to do better next time. You can take rejection—you’ve been taking rejection, but you’ve also been giving yourself rejection as your only option. Give yourself the chance at not rejection.

You say that your self-esteem is non-existent right now. Here’s a crazy truth of life: Self-esteem itself is not a great thing. Self-esteem is based on the ego and the ego is vain and sensitive and impossible to keep happy. If you base your self-worth on self-esteem, then you’re basing your self-worth on the external—what people think of you, what you have, what you’re going to get. What you need most of all is self-compassion. Realize that you’re doing some hard ass work here and give yourself credit for being willing to do it. Finding a partner is a quest and it goes through a lot of uncomfortable territory. But you’re on that quest, you’re on the search, you’re not giving up, and you’re going to triumph.

In terms of a script for how to talk about where you stand in a relationship, I want you to focus on statements. Don’t ask questions—tell them where you are. Say, “I’m seeing a few other people right now,” and see how he responds. Or, “I really like hanging out with you. I’ve paused my online dating profile because I’m having a good time and I’m not interested in also seeing other people,” and then let him respond. You aren’t asking for permission, you’re telling him where you stand.

Date guys who ask you about yourself. Scare yourself and tell them what you want. And realize that you have the power. You always have.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris.

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