Things You Should Never Say On A First Date (From Personal Experience)


I am pretty terrible at romance, but I have a few first date tips to offer you all. Why? Because I am an idiot, and have said a whole slew of idiotic things at some point. As a matter of fact, just the other day, I was on an initial outing with somebody. We were hanging out, having some wine and getting to know one another (as one does on a first date) when he started clearing his throat. Being the overly mom-figure that I tend to be, I asked what was wrong, to which he said he thought he might be coming down with something. Instead of being normal and saying, “I hope not” or “feel better” like a normal person, I wound up remarking:

“Oh god, it sounds like you have the flu that’s been going around all over the country. They’re saying this is the worst flu season in years. A ton of people have died from it.”


This was not appropriate to say. You should never tell someone on the first date that they’re dying, or might die, or have something people have died from. Just don’t do it. It makes things weird. Seriously. So as somebody who is genuinely stupid when it comes to dating, here are a few first date tips of what not to say for anybody decidedly opposed to deterring prospective partners. Some of these are quotes I’ve said, some have been said to me, but all of them should be avoided.

Photo: Walt Disney Pictures

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    • Quin

      Oh hell no, a guy cannot bash the blue hair.
      I have a chunk of blue hair at the moment, and although I haven’t had someone tell me I’d be prettier without it, I’ve had people tell me I’d be prettier if I grew my hair out, which I always thought was none of their business.

    • Lastango

      I hadn’t expected such a great list! (How’s that for a backhanded complement?)

      I agree, and I think this sort of thing is a growing problem. After all, in the era of hookup culture and social media, why would our dates think anything off-limits just because it’s the first outing?

      But for now, they should contain themselves. IMO that’s one reason why “action” dates, where the two of you do something together, are best. Then the focus is mostly on the activity or event. A dinner date is an invitation for chatter on a personal level. When you’re struck across the table from one another for two hours, there’s pressure to ask about and reveal personal information. And if one person starts sharing very personal things it creates an expectation that the other person will reciprocate — but they may not want to do that yet, so a gap opens.

      Better to get comfortable with the other person first. Otherwise both of you may feel awkward. I know I don’t enjoy listening to the intimate life details of someone who is basically still a stranger, and I don’t want them asking me about mine. Having to say, “I don’t want to talk about that” or being evasive puts a chill on what should be an experience that draws two people together. It also makes the other person feel like they’ve overstepped, and then they’ll apologize, which can kill their whole experience because they think they’be been offensive.

      In the long run, it may work out best if the info comes out naturally over time, in small bits, with each person deciding what they want to say about themselves, and when they want to say it. But that takes patience. It also takes a fundamental respect for the other person and for yourself.

      I can think of one tip to add: don’t send “needy” signals. Until there’s a personal bond, no one is looking to pick part of our burden or get us out of our messes. If other people feel like they’re being asked to sign on for that, they may not hang around long.

    • Paul

      Amanda: I found the Gloss last night and enjoy the writing. Although I’m a mid-40′s Canuck, I live by the mantra: you’re only young once, but you can be immature forever. I personally would have found your comments funny had we been on a date. Your inappropriate comment about the flu would have resulted in a counter-point on the fun one can have with bed bugs and dengue fever ( I’ve had close encounters with both). I suggest you keep doing this. You can filter out the dud guys who have a rudimentary sense of humour.

      • Samantha_Escobar

        I am actually Sam, but that is good to know nevertheless!