Dating expert: Stop overthinking everything

Answers to many dating questions are simpler than you think

This morning 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 — I’ve been one to overthink situations myself — 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:

Q: “How can I ask him about having dinner on Friday?”

A: “How about dinner on Friday?”


Q: “How could I, as the woman, do the asking? Can you give examples of the dialogue?”

A: “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.’”

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

A: “NO!”


Q: “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.’”

A: “It is confusing! You can reply, ‘Sounds good. I’m free ______ or _______ if either works,’ or ‘Is that you asking me out?’ or ‘Sounds good! Let me know what you have in mind.’”

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

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


Q: “What do you do if they reject all your ideas?”

A: “And they don’t propose an alternative? They’re not interested.”

Q: “What do you do when you get no reply to the confirmation?”

A: “If everything had already been confirmed — time, date and location — and they haven’t reached out to cancel, then you go on your date.”

Q: “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?”

A: “Did you still want to meet?”


Q: “Plans to see each other this week, but his response is, ‘When I’m free, I’ll let you know.’”

A: “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 (insert winking emoji).”

Q: “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.”

A: “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”


Q: “Got stood up. Is it petty to message him and say it was rude (in polite words)?”

A: “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 he disrespected your time is not petty. It’s empowering.”

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.

Erika Ettin is the founder of A Little Nudge, where she helps others navigate the often intimidating world of online dating.