Two Sense: Can I Have My Cake and Eat It, Too?


I'm in my mid-20s and recently hit it off with a 30-something guy at a bar. He's finalizing a divorce and has a couple of kids; I've been contemplating a break from my three-year boyfriend. He advised me to leave while I'm young, as he knew his marriage was a mistake from the beginning. We've been texting, hanging out, and we've kissed. He's enjoying the single life and acts like a guy in his 20s: last-minute plans, indecisiveness. But sometimes I think he wants more than friendship or booty because he'll act chivalrous, hold my hand, and say certain things. For my part, I don't have the heart/strength to break it off with my boyfriend right now, yet I'm flirting with this man because I've never really dated much. I've either been totally single or in a relationship. Am I delusional? Do I even have a right to ask him what he wants from me?

He Said: One of the lessons guys learn as we become men is this: If you're interested in a woman who's in a relationship, do not do or say anything to induce her to leave her partner (absent some indication of abuse). This is not some William Bennett moral BS. It's common sense. All relationships go through rough patches, and if a man has to deal not only with the issues he has with his girlfriend, but with fending off some opportunistic vulture, then none of us are safe. I suspect you ladies may have some similar best practice.

So a not-quite-divorced father of two who advises you to leave your boyfriend ASAP and hook up with him is suspicious. You need to put him on the sidelines until you finish your current relationship. Then talk with your boyfriend about taking a break. He's likely to ask if there is someone else in your life and it will be better to honestly answer no. Most of us have, at one time or another, had one in the queue before we break with the current partner, but overlapping relationships are needlessly complicated.

She Said: That's good big-picture advice, and I agree with it, but I don't think you're going to take it just because it's common sense. So let's take this down to a more personal level. This guy married a woman he knew wasn't right for him, and proceeded to get her pregnant twice before their divorce. Now he's texting and making out with a woman who has a longterm boyfriend. He makes last-minute plans and is indecisive. But he holds your hand and acts chivalrous, so maybe he really is Prince Charming come to rescue you from your lackluster relationship?

Um, no. The much more likely truth is that he's newly single and it's easy to text, make out, and flirt with you. That's all. You don't say much about your boyfriend, but it sounds like, given your young age and the fact you've never dated, the relationship is slowly coming to an end. Your new friend is correct in saying that breakups are easier the younger you are. You should heed that advice. Yet, you can't bear to part with your boyfriend right now. This, I suspect, is exactly why you find Mr. Divorced so attractive. His attention, chivalry, and the resulting hope/projection you cast on the situation, regardless of how unrealistic it may be, is in fact giving you the energy to eventually propel yourself out of your relationship. It may take a few weeks, or it may take several months, but I suspect you'll keep flirting with Mr. D until you are broken up. How far you take that flirting depends on your moral beliefs and your sense of self-preservation versus risk.

Nevertheless, you do have every right to ask Mr. D what he wants from you, just like you'd have that right with a stranger on the subway who was grabbing your ass. Your being in relationship takes away none of your rights with him. Just remember that it's probably a rhetorical question. Even if he said, "I want to whisk you away and marry you the minute my divorce is final," it wouldn't quite solve your core problem of never having dated enough, would it? You'd simply be heading straight into your next longterm relationship. No, Mr. D is not Prince Charming. He's simply a symbol, a little wakeup call that signals it's time for a change. 

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