All About Connecting: Five rules for the first date

Dear Nancy: I am recently separated and starting to date. After my first three dates, I am rather frustrated. It seems the men I date just want to talk about themselves and thus, it is no surprise that I’m never asked out for a second date. How are they supposed to get to know me if they don’t ask any questions about myself?

Lisa - 57, West Chester

Dear Lisa: This is a great question and one of the most frequent concerns I hear from clients. In order to avoid classic first date missteps such as yours, I go over five rules with my clients prior to any first date. Since one of my rules clearly tackles your concern, I will take this opportunity to share with you my “First Date Rules.”

1. Do not discuss your other dates - Period.


2. Do not talk about money – This can make you sound obnoxious, leads people to assume you’re materialistic, and can give off the impression that you’re prodding to see how much money they make or have.

3. If you like your date, be sure to secure the second date well before the bill comes. This doesn’t mean just have your date promise to call you; since it’s hard enough to align schedules and date ideas through texts or phone calls. Deciding together when and where you’d like to meet next insures less hassle and more partnership going forward.

4. To be a successful dater you should always try to make your date feel better about themselves by the end of the date than they did at the beginning.

5. (Here’s your answer) It is your job to keep up 50% of the conversation - Reread your date’s online profile so you have some immediate topics to discuss. If someone is speaking too much, feel free to jump into the conversation. If your date is non-conversant, ask open-ended questions.

Hope this helps with your next date!

Dear Nancy: I’m a 37 year-old single. Is chivalry dead? I try to open the door for a woman, take her coat, pull out her chair and stand when she approaches or gets up from the table, as I was taught to do. Instead of my actions being appreciated, the woman I am with usually gives me a weird look or asks me not make such a scene. Is it just me?

Call Me Old Fashioned- 37, Thorndale

Dear Old Fashioned: No, chivalry is not dead. However, men are challenged these days to know what manners are a bit outdated and what gestures women still appreciate. Most women still love the idea of a man holding a door open for them. When entering a cab, don’t forget to not only hold open the door, but also to ensure that your date’s skirt or coat gets tucked inside, rather than stuck in the door. When inside, nowadays, women seem in a hurry and tend to remove their coat on their own. I’ve found what works best for men is to gently offer by asking first, “May I help you with your coat?”, and then waiting for her reply. In fact, nowadays, men do best who ask the lady what she would prefer instead of making assumptions. Most likely, young woman these days will find it odd for you to stand up whenever she approaches or gets up from the table. However, the older generation will probably all fall in love with you just for that very gesture. So perhaps save the move for when you meet the parents!

Here’s to Chivalry!

Please feel free to write Nancy with your dating question. We look forward to hearing from you!

Nancy Plummer is the president and founder of All About Connecting - a personal dating, matchmaker and relationship coaching service. Contact her at or visit