Dear Jack: The 5 Do’s and Don’ts of Dating


Hey Clueless Catherine,

Last week I promised I would share some basic tips that will help you score big. Follow this outline and you should be golden.

DO - Have a game plan.

After you both fly kites, have a plan of attack. Things are going well, so suggest going to bar that’s closer to your house. This will make you seem fun and interested.

Ok, things are tanking, he continues to tell you about every girl he has “taken down” in the city since he touched down, have an exit plan in this case. Try, “my roommate is freaking out because I used the last roll of toilet paper.” It works like a charm.

DON’T - Bring bad habits to a date.

Ok, so you smoke when you drink, that’s fine.But don’t smoke while you date.

DO - Pick a good venue.

He doesn’t want to come over and get Pinkberry while watching your roommates chug down bottles of wine while watching the Bachelor.

DON’T - Talk about your exes.

Y’all will eventually cross that bridge…just not now.

DO - Look good.

Believe me, we notice, and we will appreciate it.

DON’T - Play the name game for more than five minutes.

Ok cool, so you have mutual friends. No need to keep it going on for the entire date. Recall, this is about getting to know the other person – not the other person’s people.

DO - Buy a round of drinks.

This a game changer for any guy and an easy slam dunk.

DON’T - Try and follow up immediately.

Give him some time. If he likes you, he will get in touch.

DO - Let someone know if you had a good time.

Tell him and/or them (roommates/friends), good news travels fast. If he did good work, he will appreciate the compliment.

DON’T- Look over your shoulder.

Yes, everyone knows you are single and yes, being on a date is normal for someone single.


Catherine, congratulations you now have a clue.

Hope this helps,



P.S. Keep your questions coming –

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