Make the pro a real strength, make the con a playful flaw that shows personality, and say both as a picture instead of an explanation. The danger is arrogance by accident. On a live review, a student wrote that he is very smart and might make a woman feel dumb. Our coach called it better than his other answers, because it at least polarizes, and then said it was too on the nose. You want to be arrogant on purpose, with a wink, not arrogant because you forgot how it would sound.
Arrogant on purpose, not by accident
That one line from the live review is the whole prompt in miniature. It is polarizing, which is good: our prompts lesson says attention-grabbing or polarizing prompts are the ones worth writing, because they are the ones that get read.
What made it land wrong was how plain it was. A flat claim of being smart, with the con attached as a consequence, reads as a man who has not noticed how the sentence sounds. Arrogance on purpose has some play in it. The reader can tell you know it is a boast.
Do not explain the joke
The same student wrote that he is in good shape, but his look at a woman eating donuts might be unbearable. The coach said it was too logical and too much exposition. The writer was telling instead of showing.
That is the common failure with this prompt. A pro and a con invite a tidy little argument: here is the good, here is the cost, here is why. A tidy argument is how a résumé reads. The line that works is the one where the reader sees the scene and does the logic herself.
Specific and evocative is not the same as polarizing
On another review, a student answered a similar "dating me is like" prompt with waking up to sunny skies after a week of rain. The coach said it was okay: it was specific and evocative. But it was not polarizing and it did not stand out.
Use that as a second test. Specific is necessary and not enough. Ask whether a woman could read your answer and disagree, or react with a laugh, or feel faintly challenged. If every reader nods and moves on, you have written something pleasant and forgettable.
If you cannot picture her reading it, cut it
A student on a live call asked whether his con was too wholesome. His answer was that he would pat her head and make her feel small. The coach said he did not understand how making a woman feel small is a good thing, and that he could not tell how a woman would read the line.
That is the cleanest reason to run this check: read your answer as the woman reading it. If an experienced coach cannot say what impression it leaves, a stranger has no chance. A con should make her smile at your flaw, and it should not leave her wondering what you meant.
Let the pro be a résumé line with personality
In the first review, one of the student's other answers was a boast about having traveled to more countries than the woman reading. The coach said it at least builds a résumé, but added that it should carry something extra. A bare fact is just a fact, and the line improves when it shows how you talk, not only what you did.
A list of activities has the same problem. In the same review he noted that listing what you do, such as dancing or sports, says what you do without saying you are good at it, and so it does not build anything.
Pair it with prompts that do other jobs
A prompt is not good by itself. It is a vehicle for an attractive trait of yours. The pro and con prompt is good for conveying confidence with a sense of humor, and your other prompts should carry other things: what you look for, what a date with you is like.
Write five or six answers across the prompts you like and cut to the best three. When you compare, ask which answers are strongest alone and which three work as a set. If two of your best are doing the same job, keep one and move the other to a different app.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.