So many questions I get, as a dating coach, follow the format of, “How do I ask ____?” That blank might be “for more time together,” “for a date this Friday,” “for a few texts between dates,” “what they’re looking for in the future.” And in all of these cases, I would simple cross off the “how do I ask,” and you’re left with your answer—just ask what’s on your mind!

On Instagram, I posed a query to my followers: What questions do you have regarding planning a date?

The questions ran the gamut, but the general theme was that people seem to overthink. Everything. Now, I’m certainly not judging—we’re all prone to overthinking at one time or another—but as an unbiased third party, I can tell you that things are often much simpler than we make them out to be.

Here are a few of the questions I received:

Question: We have plans to see each other this week, but his response is, “When I’m free, I’ll let you know.” What to do?

Answer: Say this: “I’m not really a last-minute planner, so let me know when you can. No guarantees I’ll still be available, though. I’m a busy lady.”

Question: I had two great dates with his guy. But last week, he didn’t text me for three whole days. And he’s rejected my last two date ideas without giving an alternative. BUT, today, he offered twice to help me move out of my apartment next weekend. I’m feeling so many mixed signals.

Answer: Ask. Start with, “I can’t tell…” When you start that way, you’re simply asking for clarification. “I can’t tell from our texts if you’re looking to go out again or not… or just be my mover. Haha”

Simple.

Question: I got stood up. Is it petty to message him and say it was rude (in polite words)?

Answer: Petty? If anyone should be worried about how they made someone feel, it’s him! Use whatever words you want. It was unacceptable and he should know it. Telling someone that he disrespected your time is not petty. It’s empowering. Why the focus on being so polite?

Question: How can I ask him about having dinner on Friday?

Answer: “How about dinner on Friday?”

Simple.

Question: How could I, as the woman, ask for a date? Can you give examples of the dialogue?

Answer: Short of just plain asking someone out on the date, here’s what I recommend: “I’m really enjoying our conversation! Should we meet this week for a drink/coffee/walk?” or “I’m really enjoying our conversation! Where should we go from here?” or “Great question! Much easier to answer in person.”

Question: If you ask someone out, and they don’t respond in the app, do you reach out through Instagram?

Answer: No. Instagram is not a dating app. If someone doesn’t respond on the app, take the loss and move on to someone who does.

Simple.

Question: As the woman, I’m so confused about how to respond and how to handle this kind of ‘not-asking ask,’ like “let’s grab drinks sometime.”

Answer: It is confusing! You can reply, “Sounds good. I’m free ____ or ____ if either works” or “Is that you asking me on a date??” or “Sounds good! Let me know what you have in mind.”

Question: Last Thursday, he suggested we meet for drinks, and I said, “Yes! How about Wednesday? It’s now Monday and no response.”

Answer: “Just checking in about Wednesday so I can get my week squared away.”

Simple.

Question: If he said three weeks ago, “Let’s meet,” but I haven’t heard back from him, what’s a good text to send to see if he wants to meet?”

Answer: “Did you still want to meet?”

Simple.

Do you notice a trend in all of my responses? I hope so. It’s that the answer is simple. It doesn’t require overthinking, mincing words or second guessing. It simply says the words you want to say. Can we control how someone will react to them? Of course not. All we can do is ask what we want and put ourselves out there.

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