As a professional matchmaker in NYC, I have set up thousands of first dates. I have also collected thousands of dating feedback forms from clients (and matches) after the date. After nearly 10 years of matchmaking, I am basically an encyclopedia of what kind of bad dating behavior will ensure you never go on a second date. Dating is an art form. And if you do it right, you’ll acquire a masterpiece of a relationship. Here are the five things a man should never do on a first date.

Talk about an ex: If it’s a funny anecdote, then I suppose it’s fine. However, if you’re going to talk emotions, needs, and unresolved issues, leave it at the door, because right now, for the sake of the first date, you need to figure out if you’re compatible. You don’t want to come off bitter or jaded.

Go straight to the date after work: All that crazy aggressive work mood energy you have is just going to be too heavy for a first date. You need to shift your work energy to date energy, and that decompression will never happen in the 15 minute cab ride to the date venue, while you scroll through your work inbox answering any last emails. Give yourself thirty minutes to just chill. Walk around, grab a Starbucks, *ahem* freshen up, and think happy thoughts. Get into dating mode for better dating experiences.

Mansplaining. She’s an expert on living her own life, and your anecdotes to her experience is going to make her feel defeated. Ask questions, listen to her answers, and let her expand. Women just love it when they feel listened to.

Being awful to waitstaff. Condescending attitudes don’t get anyone far. Remember your please and thank yous.

Not dressing the part. You’re on a first date, not the floor of the NYSE. Wear a tailored suit (take off the tie) or well fitted jeans, shirt and blazer. Your shoes should be clean and made of leather. The belt better match the shoes. Your cologne should only be detected if she is giving you a hug. Your wallet should not be coming apart at the seams or velcro. (And it should be ready to pay for the first date.)

Learn more about Maria Avgitidis’s matchmaking services by visiting or calling 212-363-0486 to schedule an in person consultation.