“If you don’t know, ask.”

I find myself giving this advice on an almost daily basis.

I got a text recently from a male client who had met a woman at a party the previous weekend. She promptly found him on Instagram and suggested meeting. (Good for her for taking the initiative! How would you feel about that?) He then asked me if he should consider it to be a date. I told him that I thought it was, but it might not be a bad idea to say, “I’m looking forward to our date,” to be abundantly clear. (He did not take this advice.) A few days later, he sent me this:

“Kind of in a pickle now. She asked if another mutual friend can join us. I think this is bad! It probably is a signal that she doesn't think of this as a date nor want it to be. What should I say to her??”

I’ll admit that, no, it doesn’t sound promising. But, rather than making an assumption, whether correct or not, it’s best to go straight to the source. My response to his question was, “I would ask. I know that sounds scary, but it's the only way to know. Say something like, ‘I was actually looking forward to getting to know you one-on-one, like as a date. Not sure if that's what you had in mind, so I just wanted to clarify.’ I know you have it in you!”

To be honest, I don’t think he’ll ask (strike two for taking my advice), not because he doesn’t want to know, but because he doesn’t want to somehow jinx his chance of it being a date (even though I believe she had already made up her mind). Or, if she says it’s not a date, he’ll feel rejected, and he would prefer the uncertainty than the chance of a certain “no.”

This happens all the time, and not just in dating. We assume things about people — why they called, why they didn’t call, what something means, what something doesn’t mean. Sometimes we’re correct, and other times we’re way off. The only one sure-fire way to get your answer is to ask. This often means 1) doing something outside your comfort zone and 2) opening yourself up to hearing something you don’t want to hear.

A friend of mine, Sonia, had been seeing someone for about three months. She thought they were entering into relationship territory. I asked her one day if they were exclusive. She replied, “I think so.” Not good enough. I followed with, “Do you want to be exclusive?” to which she replied that she did. When we dug deeper, she revealed that her new beau mentioned early on that he wasn’t seeing anyone else. OK … well, what about the month after that? Just because he wasn’t seeing anyone else at that time doesn’t mean he wouldn’t plan on it. They had never agreed not to see anyone else.

I next encouraged her to have a talk with him about the direction things were going. Sonia was scared… less scared about the conversation itself (though bringing it up can be nerve-wracking) and more scared that the answer from him would be “no.” Both of those fears led her to accept the status quo (and, as I always say, you get what you allow) for much too long, until she finally learned that he was not, in fact, looking for a relationship.

In dating (and in life), the only way to know someone’s motive or the answer to an unanswered question is to simply ask. It’s true that you may not get the response you want, but in the long run, that’s better than continuing to be in denial. So, while asking difficult questions of someone you like might feel uncomfortable and scary, the thought of going through a situation while always being in unknown territory is much worse. In the end, it’s better to ask than to assume.

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