What are the best plans for a first date?

First you should meet your perspective date for a brief introduction to determine you both are interested in dating one another.

Blind dates are not only awkward, but can be challenging to determine a good location when you really know very little about each other. So, you could meet for a glass of wine or cup of coffee to "break the proverbial ice".   This will avoid ruining an opportunity to date someone you like because he made a bad impression on the first date.

Once you know a little about your date, you will want to choose a location that suits you and your date's personality and interests.  If your date lives a healthy and energetic lifestyle perhaps you could choose a park and have a picnic.  If you both have an interest in literature or art, you could visit some museums or bookstores that specialize in either and then a dinner afterward.

The key is to show a genuine interest in the other person by knowing her likes and dislikes then planning accordingly.  You don't need to go overboard, just be conscientious of your plans as they would appeal to your date.

I asked a co-worker if she would like to go to dinner and she accepted.  I didn't indicate it was a date, but I am hoping it will lead in that direction.  Should I pay for the meal or see where things go when getting to know each other as friends?

Since you extended the invitation then you should pay for the meal regardless of your intentions for a romantic relationship in the future.  If she appears to be upset that you are paying then you can tell her she can pick up the tab on your next time you go to dinner.  This may give you an opportunity then to discuss a second dinner or lunch.

Are there things you should not do on the first date?

Absolutely!  This date should be about getting to know more about someone in an environment ideally suited for both of you.  However, enough can not be said about expanding too much on your past relationships, problems or personal issues.  It's not a confession nor is it a counseling session, so keep the topic of conversation light and fun.  Ask a lot of questions but don't grill your date on his background or goals.  You're not really interviewing him, but you could ask some decent questions like where do you see yourself over the next few years?  Those types of questions can open the door for hobbies, career, family, commitments, etc.

Don't provide too many details about issues of a personal nature. 

It is usually a bit too much for most first dates and it's better to wait until you get to know someone before you share private details about your life, family or situation.  Even if you have a keen sense regarding the intentions of others; it is possible that some people have bad intentions and you won't want this information about yourself in the wrong hands.

Don't drink too much or get too carried away.

It's great to have fun; but unless you want him running for the hills, don't party like a rock star.  It won't be an attractive side for him to take care of you because you had too much to drink and need to puke in a trash can behind the bar.  Also, it is never a good idea to get intoxicated to the point where you may not be able to make responsible decisions or maintain your safety while with someone you do not know very well. 

Don't meet at a private residence.

If you are meeting for the first few times, never ever meet someone at a residence, a party, hotel room or any private location.  Keep the first dates in a public place like a restaurant or museum.  It can be anywhere there are numerous people and not just friends of your date.  Date rape occurs most frequently in a private residence and the best way to protect yourself from such a crime is to avoid giving these criminals an opportunity to harm you.

Don't be afraid to have fun.

In a world where we should be cautious of strangers or new relationships after a painful break-up it may seem as though everyone has bad intentions.  Use your intuition, but don't let go of your common sense.  If things are going well and your hitting it off; don't be afraid to let go a little bit.  Just don't be swayed away from making good decisions to stay safe.

I met someone on-line and he is taking me to a surprise restaurant.  What should I wear if I don't know where I am going?

First of all, never go anywhere you don't know with a stranger.  You should know exactly what he has planned for the date.  You should then provide his contact information, where you met and planned dating location to a close friend before the date.  You should be familiar with the general area where you too will be going and for extra precaution it is best if you meet him there the first few dates instead of him driving.

A great way to find out where he plans to take you is to tell him you will need to know where you are going so that you can dress appropriately and for your personal safety. 

If he doesn't understand that, he may not be a good dating candidate or just a complete idiot.  Either way, don't go.