Ask Anna: Navigating casual dating when she wants more

Anna Pulley, Tribune News Service on

Published in Lifestyles

Dear Anna,

I'm a guy in my late 20s, and I'm not on the lookout for a lasting relationship at the moment. I'm enjoying the freedom, exploring my options and focusing on personal growth. Recently, I've started seeing this fantastic woman. She's got all the great qualities you’d look for, but here's the rub: She's interested in something serious.

From the get-go, I've been transparent with her about my stance on relationships right now — that I'm not ready to dive into anything deep and long term. She seemed OK with this and keen to continue dating, regardless. However, the more time we spend together, the more I can sense that she's holding out hope that I'll change my mind.

There’s this nagging thought inside me: Would it be wiser and more ethical to break things off now before we weave ourselves into a complicated mess later on? I don't want to lead her on, but I also enjoy our time together. What’s the right move here? — Bent About Not Destroying An Innocent Damsel


Kudos to you for not wanting to be the inadvertent villain in someone else's love story. It speaks volumes about your character that you're considering the ethical implications of this situation.

I used to be of the mind that honesty was honesty and if one was transparent with their romantic partners, then the work was done and one could rest easy. And then, after I unnecessarily hurt several people whom I did not want to hurt using such a strategy, I reconsidered my stance.

This isn’t to say our situations are the same or that people aren’t allowed to make their own choices in the matter, but let’s break it down.

First, as we’ve covered, you've done your part in the arena of honesty by being upfront about your intentions — or, in this case, the lack thereof when it comes to any kind of long-term commitment. Great! She's heard your speech, nodded her understanding, and decided to carry on with the hope that maybe, just maybe, your “not now” could turn into a “let's see where this goes” somewhere down the line.


Let’s assume also that this fantastic woman is an adult and that she's made her choice to carry on, eyes wide open. So far so good.

What you need is a recheck — like a doctor reassessing a patient after the initial prognosis. Sit down with her again and have The Talk, Part Two. (Frankly, such conversations should be recurring in any relationship, but especially those where the waters are murkier.) She needs to fully understand that your “I’m not ready” is not code for “Convince me otherwise” or “Wait until I've had my fill of fun.”

In this heartfelt encore, gently remind her of your current stance. Make sure to listen as much as you speak to ensure that not only are your thoughts heard but hers as well. This will give her space to voice her feelings and perhaps face her own expectations head-on, without any rose-colored lenses of wishful thinking — if she’s experiencing that.

If, during the check-in, you sense that you’re not on the same page, or her hopes for a “more” are resounding, then it’s likely time to retreat. Continuing to see her, in that case, might drift into the realm of leading her on, even though that is not your intent.

A good rule of thumb here — and an unwritten rule in the modern dating handbook — is that one should avoid igniting the flames of romance when one knows that they intend to douse them soon after. Tough, I know, but it’s a kindness in itself. If you're certain that the line in the sand you've drawn for your relationship readiness is deep and definitive, then you should brace yourself for a goodbye that might feel premature but ultimately prevents a harsher heartbreak down the line.

In all this, take stock of your feelings too, since self-reflection is never a one-and-done deal. Are you absolutely sure a relationship isn't what you want, or is it that you don't want a relationship with her? It's a question worth pondering as you weigh your options and examine the horizon of your emotions.

Ending things may not be the easy choice, but it could well be the compassionate one. And sometimes, the most genuine form of respect and affection we can offer someone is not the story they wish to write with us, but the truth they need to hear from us instead.

Whatever your decision, remember to handle it with the grace and respect you've demonstrated thus far.

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