Brad, Author of The 21st Century Guide to Bachelorhood, Speak Ups.

Q: What do you love most about living in a city like New York?
NYC is the most exciting city in the world. The sports, concerts, shows, movies, clubs and restaurants are the best in the world. The city is a melting pot of nationalities so the people are very interesting with diverse backgrounds.

Q: As great as New York is for singles, many people find it extremely difficult to meet new people. In your opinion what are some of the best places to meet people of the opposite sex?
You can meet attractive girls just about anywhere in NYC, you just have to leave your inhibitions at home. You can meet girls walking down the street during lunch hour in vegetable markets in Union Square, or at your favorite restaurant. Bars are great places to meet girls, but try to meet them before either you or she has one too many, lol. Also, better department stores, like Saks and Bloomingdale's, have loads of attractive women in the perfume and makeup areas. The gym is a great place to meet women, try to take an aerobics class or just try to sit next to somebody that is on the bike or treadmill. Charity parties are great places to meet girls, the people are usually dressed nicely and want to meet people. Try web-based dating sites like Match.com, EHarmony or JDATE. But if you do that, be honest with your self assessment.

Q: What inspired you to write your book, The 21st Century Guide to Bachelorhood: Lessons Learned Over the Past 20 Years?
I started writing this book in 1999 because I just had so many bad dates and had many funny stories. The book was 80% completed by the end of 1999, but then I started a new career at a hedge fund and just didn't have a lot of time to finish it. In fact, I had 3 books 80% completed in 1999, the other two are: 1) a book about 3-time world champion boxer Iran Barkley, which I plan to finish by the summer, and 2) a sci-fi thriller which I plan to complete by the end of the year. I left the hedge fund business in September and am now working for a couple of sports marketing companies. I have much more free time now than I did when I worked on Wall Street, so it allows me to complete my books.

Q: What are some of the biggest faux pas women make when it comes to dating?
After a first date, the woman should let the guy pursue her a little. I believe that a guy should be a gentleman and call her if he wants to see her again. Many women get obsessed very early in a relationship and sit by the phone waiting for a guy to call, or even call a guy incessantly very early in a relationship. Girls should allow the guy to call and make the plans. If he calls, great. If he doesn't, he is not interested.

Q: How do you think the media has affected single men given the commotion around chick lit and movies like Sex and The City?
When the book The Rules came out, women thought that following 'the rules' was a way to attract men. It wasn't. Guys lost interest in girls that did those foolish things and many girls went dateless on Saturday nights. There are many chick lit books out there, none of which I have read. Sex and the City brought empowerment to single women, especially in NYC. I think the show and movie impacted retailers, restaurants and clubs more than it affected the way women related to men.

Q: There are plenty of online dating sites such as GoldDigger.com, Milf-date.com, that try to help individuals find wealthy mates.  Given the economy, what do you think about the message these services are sending?
Hey, if that is what people are looking for, who am I to judge them? I do, however, ask these women, "what do you bring to the table that makes you such a great catch as to demand a millionaire? Is money the most important thing in a relationship?" Personally, I think love, friendship, integrity, and mutual goals are much more important than money. Those are the things that make the 'cake.' Money is icing on the cake. But without the cake, you have nothing.

Q: How can today’s bachelors spot and protect themselves from gold digging women?
When women ask you what kind of car you drive, how much money you make, where you 'summer' too early in the relationship, especially if its on a first or second date, a red flag should go up. I know a woman who had no money, a low paying job and had her parents pay her rent. She refused to date anybody who was not a millionaire. What an awful attitude!

Q: Best spot for a first date?
A first date should be casual. If it's a blind date, it needs to be a drink or cup of coffee, and no more than 45 minutes. A guy will know very quickly if he wants to see this girl again. Girls tend to make those decisions a little later in the date or relationship. If the date is going well, a guy should walk her home after the date and ask to see her again. If he didn't like her, he should walk her home and just say goodnight.

If the two have met before, then dinner is fine. But it must still be casual, not too loud, and not at a romantic restaurant. The first couple of dates are all about getting to know somebody gradually.

Q: What about a cheap but impressive one?
The money spent is irrelevant, as long as both parties have fun. You can have a great date just walking around the Central Park Zoo, but have a horrible date at an overly priced restaurant. It is all about the company.

Q: What's the biggest mistake single men make when it comes to meeting women?

They don't show complete interest. They will meet a girl and wait a week to call. When they first call, they will not have a game plan for the date. They also sometimes fail to confirm the date till very late in the afternoon.

Q: Do you think women and men can/should be friends after a break up? Why or why not?

Only if they didn't date for too long. If one or both of them were hurt by the breakup, it is unlikely they can be friends.

Q: What are some first date mistakes every single guy should avoid?

Make sure to have a game plan. If you like her, don't wait a week to call her. If you don't like her, don't say at the end of the date, "I will call you."

Q: For many, the pick-up line is the hardest one to come by. Any conversation starters you would recommend when approaching a stranger?

Pick something original. Compliment her shirt or earrings. Don't say something stupid. Make her laugh.

Q: Many people get to a point when they simply hate dating. How do you suggest they adjust their attitude?

They aren't going to meet anybody unless they date. Dating can be like continuous job interviews. Perhaps they can better screen their dates before accepting them. Don't go out on a million blind dates. Don't accept dates just for the sake of having a date. If your gut says No, then don't go out again with him/her.

Q: Best Online dating tip you offer to bachelors?

Keep your introductory letters on point. Don't send out the same letter to all girls. Make sure you reference something in their profile. By doing that, you will show them that you have actually read their essays and have interest in them for more than just the photos.

Q: Please tell us how nice guys can finish first…

They oftentimes do. Have a backbone, don't let people take advantage of you. But, always be nice. Take good care of a lady, they will do the same for you. If they try to take advantage of you all the time, she isn't right for you.

Q:  How you keep and decorate a home says a lot about a man. What are some bachelor pad must haves that will make a good first, second or overnight impression?

Stylish clothes. Nice furniture. Clean apartment, especially the kitchen. Have some kind of art. Avoid the sports themes. Nice paint job. Some nice lighting. Nice entertainment center. Stocked kitchen.

Q: How can a guy who’s not good at flirting get good?

Practice. Perhaps call a girl friend and practice with her. Go out to random bars and flirt with a few girls even if not interested. Learn to read the signals.

Q: Secret sex tip every man should know about

Oral sex is the key to a woman's heart. Hey, she does it to you, make sure you please her as well.

Q: Taboo topics in the getting to know you phase

Overt sex talk, politics, controversial topics.
Q: Any other words of wisdom?
I have never been a fan of blind dates. I wrote a whole chapter about it in my book: The 21st Century Guide to Bachelorhood: Lessons Learned Over the Past 20 Years. People tend to introduce their friends to people they think are nice or good looking, not what their friend would necessarily like. All women think their friends are beautiful and guys never know when their friends are good looking. Should somebody decide to do a blind date, it must be kept at 45 minutes, tops. Be a gentleman at all times. And don't feel weird if you arrange for 2 blind dates in the same evening. For details, read the book!  ;-)