Dear Tamar,

Can you please help me to find a way to start a conversation with a woman? Can you please tell me what subjects I should, or should not, talk about at the first meeting? Thanks in advance!

Dear Conversation Starter,

Great question! There are some cute ‘n catchy lines you can use to start a conversation. These include,  “I didn’t know they made Jews like you!” or you can just go the straight forward route with,  “Hi, my name is Tamar it’s nice to meet you.” To be perfectly honest, if a girl is interested it doesn’t matter what you say!

As for conversation topics to avoid, don’t discuss any baggage. Baggage includes past relationships, dramas, illnesses and other types of negativity-inducing subjects. Instead, concentrate on discussing positive topics like the things you have in common — your hobbies, favorite foods, pets, etc. And if you find the conversation could keep going all night, then parlay that into a second date!

Julie* recently went on a 100hookup with Brian, a good looking lawyer who recently moved to town. Unfortunately, the report was not good. Yes, Brian was handsome and smart, but no, he’s not an avid conversationalist. This guy didn’t know the meaning of biting his tongue or having restraint — he was an open book but Julie had barely read the back cover. The more he told Julie about himself, the less interested she became.

Brian proceeded to tell Julie all about his entire life over the course of one drink and one hour: his father’s six ex-wives; the medicines Brian takes for OCD and ADHD; his dyslexia; his skin rashes; his likes and dislikes; and finally – the kicker – his ex-girlfriend. None of the items are particularly funny when heard separately, but when taken altogether it was a dark comedy that had come to life.

Maybe Brian was trying to put all his cards on the table and let Julie know exactly what she’s getting into, but his technique needs some major help. Of the above list, the only topic that should be discussed during a first date is your likes and dislikes. 100hookup makes you feel like you know someone better than you really do before you even meet, but remember that the person sitting across from you is still a stranger. The prescriptions in your medicine cabinet are not something you would discuss with the person sitting next to you in the doctor’s waiting room, so why share it with a girl you’re trying to impress?

One of the reasons I suggest meeting your 100hookup matches right away is because you need to maintain some semblance of normalcy when it comes to conversation. You have the topics right in front of you when you look at their profiles, so use it to your advantage and keep to the typical first date conversation topics within those guidelines: why did you choose to go to [college]? Where did you grow up? How did you get started in your career? Stick to the basics and censor yourself before divulging information that is, to put it bluntly, none of your date’s business right now. On the first few dates, regale your date with funny, positive and interesting stories about yourself and leave the deeper, sad and bewildering stories for later on in the relationship. Hopefully you will be charming enough with the former to leave plenty of time for the latter.

*all names have been changed

Dear Tamar,

I am so incredibly puzzled. I have gone on numerous dates that all seem really great. They’d last an average of 2-3 hours for dinner. My photos are completely accurate and updated.  In fact, I am often thanked for being so honest. I am 48 and look much younger (and awkward to say about myself, but I am considered very attractive). I have teens and am dating men around the same age as me. I have been completely puzzled because I am not being called for second dates by those I would like to have a second date with. One recently texted 30 minutes after the date to say he had a great time…and then no follow up. I am really confused and feel like shelving dating.

Dear Ready to Give Up,

Don’t shelf dating just yet. I look at this from a “so far, so good” perspective: you obviously have good photos (and look like them!), you have a lot of life left to live and the men are spending a pretty big chunk of their time with you. If you remember dating the first time around, you’ll recall it wasn’t easy then either. And now you’re bringing age, experience, kids, and all the pluses and minuses that come with that to the table — and probably so are the men you’re dating. So what’s the problem? Why aren’t you getting 2nd dates?

I think what you have to look at are the conversations you’re having on the dates: are you talking about yourself and asking questions about your date? Or, are you commiserating about your past relationships, the stress of having teenagers and so forth? Although these topics may seem like bonding conversations and you may think that by putting all your cards on the table the man will know what he’s getting into, these topics also have negative connotations and may not leave a man thinking he’s had a great time.  Instead, he may think he’s left a therapy session.

Once you meet someone you like you’ll each have plenty of time to discuss your past, but right now you should be talking about upbeat, positive subjects. What interests and hobbies do you have in common? Play hookup Geography (but don’t talk badly about anyone, that’s bad karma). Talk about what you’re both looking for in the future. I believe if you stick to these topics on 1st dates you will start landing some 2nd dates. Just don’t give up, it will happen! Good luck!

One of the reasons I suggest meeting your 100hookup matches right away is because you need to maintain some semblance of normalcy when it comes to conversation. Since you’ve divulged more information than you would typically about each other in your profiles, too much emailing and phone calling will only make your actual first date feel much more serious than it actually is. Stay within the parameters of the questions asked in the 100hookup profile so that your first date doesn’t feel (or proceed) more like a 3rd date — since it isn’t.

Instead, ask for details about the fill-in the blank questions and multiple choice questions — Why did you choose the university and the major you did? Why did you pick the career path you did and is it what you wanted to be when you were growing up? Where did you grow up and how did you pick where to settle down? Stick to the basics and censor yourself before divulging information that is, to put it bluntly, none of your date’s business — at least not yet. On the first few dates, regale your date with the funny, positive and interesting stories about yourself and leave the deeper, sad and bewildering stories for later on in the relationship. Hopefully you will be able to charm enough with the former to leave plenty of time for the latter.

I have heard over and over one of the most uncomfortable parts of a first date is the conversation aspect.  Even if we are self-assured and really looking forward to the meeting, a first conversation can raise anxiety levels to a heart pounding level.  These tips for conversation starters can really help those of us who want to have a great first date.

What do you do?

What is your area of work?

What are your hobbies?

Where is your favorite vacation spot?

What is your family like?

What do you do to relax?

What do you do for fun?

What was the last book you read?

What was the last movie you watched?

What is your favorite television program?

If you could live anywhere, where would it be?

What type of music do you like?

Where did you go to school?

Where were you born and raised?

These questions are benign enough to not scare anyone away, but they also can give you some insight into what the person sharing this experience with you is all about. Remember to pay attention to body language, relax and enjoy yourself!