I know for the last 40 years women have been working towards complete equality with men, but many of us remain traditionalist outside the workforce. Recently, a guy was complaining to me about the fact that it is always expected that he will be the one to ask a woman out, and that he should be the one to pay. The conversation went on far longer than necessary, and I learned way more than I ever needed to about this guy’s life. I wish I could reclaim the lost time, but maybe that talk was not in vain, if I can use it to help some others out with some basic dating guidelines, so here we go:

1. Most women are going to expect that if a guy is interested, he will ask her out.
If she agrees to drinks, coffee, whatever, and the man likes like her, it is proper manners for the man to pay the bill. Then within 48 hours, the man should follow up with an email, text whatever, saying he had a nice time.

2. If a woman likes a man after the first date, she will respond and will make time to get another date on the calendar within a fairly reasonable time.

3. During the first few dates, look to see if you are taking turns sharing the basic information you need when checking for compatability. It is not just about chemistry, which is key, but also do you connect when you talk about one another’s backgrounds- family, education, work experience, interests?

4. After the first two dates, you should try to do an activity together– not the X-rated kind. For example, try going to a concert, movie, museum, or go for a bike ride or hiking together. We can all be on our best behavior for a few hours, but spending a longer amount of time together is a great way to gauge how well you hang for extended periods of time.

5. Be sensitive to each person’s time constraints, other responsiblities, and need for space and time to process his/her emotions and proceed at a comfortable pace. Especially if you are dating a professional, who may have children and other family obligations, you cannot expect to rank as a priority anytime soon in that person’s life.

Finally, the best advice I can give anyone is to just have fun playing 20 questions. Think of dating as a social experiment– you are learning about others, and in the process about yourself, including the things you like and don’t like in a partner. Each date hopefully brings you that much closer to finding the right one. And for the guys who think they have to do all the tough work, let me just say this– I wish I could just pay $20 for a haircut. I wish all I had to do was take a shower before a date, without having to worry about makeup, jewelry and finding that perfect outfit with the perfect shoes and handbag to match. If you would rather pick up the tab for all those other expenses, I will gladly pay the $20 for a round of drinks, otherwise stop complaining and just be a man– and open the car door.


By Regina A. DeMeo, Esq.