What Should I Say to Men Who Ask Me Out While on a First Date?

I’m back into dating after a 20+ year marriage, having read and implemented your valuable advice in Finding the One Online.” Even though I’m in my mid-50s, grossly over-educated, and live in a small town, I find I have plenty of potentially-compatible men who are expressing interest in me. So, thank you, Evan, for that!  

My question is about how to say: “you’re great, but not for me” face-to-face at the end of a first date. (I expect this is something many women struggle with.) I’ve have ‘scripts’ for most situations where I want to say “no, thank you” in writing. This makes it easy and relatively painless to be clear, polite and compassionate. And if a real-life connection develops with someone who, over time, I decide isn’t right for me, I know how to handle that in person.

But what about when I’ve been following your advice about how to have a great first date — relaxed, engaged, smiling, being open to finding the best in a man, appreciating his “putting on a show,” as you put it (and I feel I do this well, and enjoy doing it) — and at some point in the evening he asks to see me again, but by this time I know he’s not for me?

He understandably feels I’ve been having a good time, and I usually have been. Then, feeling like a deer in the headlights, I fumblingly say something that makes the situation more uncomfortable than it probably needs to be. Or, worse, I end up giving the impression I may go out with him again, because he’s caught me unprepared. If he’d waited until the next day to contact me, I’d have known exactly what to write. But what’s a friendly (though unambiguous) way for me to make the transition from “making it the best first date I can” to saying “I don’t see us as a couple,” in that sudden moment face-to-face?


As you may know, I have a problem with the truth: I always tell it.

You know who also always tells the truth?

My five-year-old son, who pulls up my shirt, points and laughs, “Daddy’s Big Belly!”

So yeah, the truth, while honest, can rightfully be viewed as tactless or blunt.

Your question, Margo, is essentially about tact. Specifically, how you can be tactful to a man who put you in an uncomfortable position.

My answer is 180 degrees from the one I gave to the woman who put her boyfriend in the uncomfortable position of telling her she’s hotter than Angelina Jolie.

Ready for Lasting Love?
Ready for Lasting Love?

Lie, Margo, lie!

As you may know, I have a problem with the truth: I always tell it.

As a passionate advocate of honesty and direct communication, this may seem dissonant, but the truth is, it’s not about “right” or “wrong,” but “effective” or “ineffective.”

I once had a woman tell me at the end of our date that she wasn’t attracted to me.

She might as well have kicked me in the nuts.

That’s how crushed I was to receive that information in that fashion on the date.

I understand; she was doing what she felt she had to do to avoid sending mixed messages.

The problem was that I was scarred for a few weeks afterwards.

So, perhaps the best way to approach this — like most dating advice — is to flip it around.

A guy goes out with you and is not attracted to you.

Is there any value of him telling you he’s not attracted to you while you’re together?

No, there is not.

The best way to end a date with a person you’re not attracted to is with a little white lie.

The best way to end a date with a person you’re not attracted to is with a little white lie.

You hug goodbye, you say you had a great time, and you say you’ll talk soon.

You don’t mean it, but it’s a polite way to end the night.

But wait, doesn’t that give the impression you may go out with him again?

Yes, it does.

But it sure beats the alternative: emotionally kicking him in the nuts with your truth.


He gets to leave the night with hope and dignity.

You get to leave the night unscathed.

The next morning, you can send a short, honest email that explains what you didn’t say in person:

“Thanks so much for dinner last night. I had a really nice time getting to know you and very much enjoyed your company. I just didn’t feel there was enough of a spark to continue a romantic relationship. But you seem like a great catch and I’m sure you’re going to make someone very happy one day. All the best in your search…”

That’ll usually do the trick.

But if a guy is pushier on the first date, and won’t take “I had a great time, let me check my schedule when I get home” for an answer, you have no choice but to lower the hammer.

“Sorry, I’m just not feeling it,” will give him the not-so-subtle hint that this is your last date.

I know it sounds weird to advocate for lying, but, in general, being polite (while remaining true to yourself) is a good impulse to have when you have someone’s heart in your hands.

If you disagree with me — if you think that honesty is ALWAYS the best policy — please understand, I’ve coached a lot of women who want men to be honest with them:

Just tell me you’re not attracted to me!

Just tell me you want to sleep with me but not commit!

Women claim to want this level of directness, but I have never heard an actual instance of such a conversation going well. Which explains why men usually don’t say such things.

Instead, they say, “I’ll call you,” and then don’t call, which, to me, seems like the kinder path than telling you the truth on the date.

Take it from a guy who has had “Good luck” said to him after more than one date.

I would have liked the illusion of going home with hope instead of having it crushed in front of my face.