You sit indifferently at the restaurant across from a woman you swore you have seen before. Have you been set up on a blind date with someone you actually went on a date with long ago but can hardly remember, or have you been married to the same woman for so long that your brain reorganizes itself every time you look at your spouse to prevent yourself from committing suicide long enough to enjoy this wonderful dinner at Olive Garden?

If you chose option number two, then it is high time to file for a divorce. If, however, you are not married, then the separation should be relatively simpler. However, do not mistake comfort for misery. That is, if you’ve been in a relationship for years, and are only in it because you work a minimum wage job and your significant other is a lottery winner, it’s time to cut them loose. In an anecdote that probably resonates with more people, don’t stay with somebody simply for convenience. This is good advice unless, of course, both you and your boy/girlfriend are boring. Then you’re screwed.

What I don’t understand however, is the ongoing relationship between a highly exciting person and someone who is dull. What are you doing? You have a lifetime of adventure that you’re just wasting so that your conservative parents will be happy. Or, is there a deeper dynamic that has already existed between your uptight parents? Maybe one day, long ago, they were exciting too, but gave up their hopes and dreams and international differences in order to appease somebody as well.

Was this originally about when it’s too late to break up? Was I originally supposed to give advice?

Dear Tamar,

I am about to be divorced. When I start dating and my date enquires why I am divorced, how much does one tell them before they are put off? My soon to be ex husband is a substance abuser and ruined our lives. Do I go into detail about this or not? Will it reflect badly on who I am? Please help!

Dear Divorce Drama Disclosure,

You don’t owe anyone an explanation. You only need to say that you’re divorced and that’s it. When it gets serious with someone then you can go into detail and divulge your past, but for now keep it to yourself. Your ex’s problems don’t make you look bad because it has nothing to do with you and I hope that you don’t let it effect your confidence as you begin a new chapter in your life. Not every guy is a substance-abusing jerk who wants to hurt you and I hope you’re open to eventually trusting a new man.

Dear Tamar,

I am having difficulty meeting men in the city of Boynton Beach, FL where I live and I’m not a barfly.  So, I’m turning to JDate for a little help. I have been divorced for 5 years now and am definitely ready to be your next success story! Could you please give me any helpful advice/tips on how to make this a successful dating experience?  Do I need to make the first move?  Should something in my profile be changed? I would appreciate ANY advice/help to make this successful and a fantastic experience.  I will be joining within the next couple days. I look forward to hearing from you and thank you in advance for your help!

Dear Next Success Story,

I appreciate your eagerness to seek help. I know you’re not a barfly but find out when there’s going to be JDate event in your area for starters. Be honest about your divorce both on JDate and on dates but don’t give too much information too soon. Keep the details to a care minimum. Once you create your profile, go through all of your matches and start using the tools to Flirt! and so on in order to let the guys know you’re interested. Make sure you’re preferences are realistic but not too narrow. I think you’re enthusiasm will help you land a lot of dates quickly!

Dear Tamar,

I feel that I receive limited responses to my JDate profile and was wondering ways to attract women? I am tall with diverse interests but divorced (no children) and in my mid-40′s. Any suggestions?

Dear Great Catch!,

You are, in fact, a great catch based solely off of the information you just gave me. I know of dozens of women who would be interested in you! So that means you’re probably not representing your best self in your profile since you’re not receiving replies. Try taking new photos – this New Year’s is a great time to get some candid photos of you having fun and celebrating! Make sure your preferences are realistic. I know women in their early to mid-thirties who would be interested in you, but you will, without a doubt, have more luck with women in their late thirties to mid-forties, so your age range needs to be pretty broad. Finally, although I’ve now told you that you seem like you’re a great catch, make sure your About Me paragraph doesn’t come across as cocky. Nothing is worse than a guy who is a great catch and says so himself! Oh, and instead of just saying “diverse interests,” actually name some of them that are indeed diverse. Having broad preferences is good, making broad statements is not.

Hi Tamar,

In your August 23rd column entitled “What’s TMI?” you advocate withholding information – such as being divorced – from one’s profile or introductory email, as it is “too much information” (TMI) and you seem to suggest waiting until you’re already making plans to meet to mention it for the first time.

While I think I understand your rationale and agree that it is unnecessary to ‘tell all’ at the outset, it nonetheless smacks distinctly of being dishonest, or at least less than candid – which is hardly the right way to kick off a potential relationship. I’m specifically speaking to divorce. Can you clarify?

Dear TMI Clarify,

I appreciate your response. I’m not telling anyone to lie. In fact, people who lie in their JDate profiles abhor me because they’re going to be found out eventually. In the specific letter you are referring to, the woman was recovering from a major surgery and in that specific case I didn’t feel it was necessary for her to use her “About Me” paragraph to talk about it, though I did advise her to tell her dates on the phone prior to meeting.

As for divorcees: If you’re divorced, separated or widowed, you most definitely need to be honest and check the appropriate box. My advice is simply not to get into all the gory details about your previous marriage — or even about previous relationships if you’ve never been married — in your “About Me” paragraph until after having been on a few dates. And as I said in “What’s TMI?” this rule goes for anything pertaining to drama in your life. For those previously married you should absolutely not lie as it is a part of your life and forever will be. But spending two hours talking about your divorce and how the children are handling it is simply not romantic nor does it allow your date to get to know YOU. I hope I’ve cleared things up!

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 Jewish 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!

Dear Tamar,

About 7 months ago my husband admitted to me that that “he didn’t think he wanted to be married to me for the next 20 or 30 years.” We’ve been married 18 years with 3 beautiful teenagers who were the focus of our marriage. He moved out 6 weeks ago and we’re at the beginning stages of a divorce.

So I’ve been betrayed, and rejected, and now my family needs to find a new normal. I want to date now even though people say it’s too early, but I’m lonely and want to do things with someone. So I signed up for JDate but I don’t know how to proceed. All I know is I don’t plan on or want to talk about my divorce while on a date.  Any advice?

Dear Divorced & Dejected,

Whew! You have had a heckuva ride these past few months. It sounds like you have a lot of healing to do but I can understand your need to be with someone… you haven’t been alone in 18 years! On one hand I think some real alone time will do you some good and on the other hand I think some real fun rebound dates where you’re made to feel wanted and gorgeous is good for the soul as well.

My advice to you regarding JDate is this: select divorced in the “current relationship status” box and under “what type of relationship are you looking for?” you should check “an activity partner,” “a date” and “a friend.” At this point you don’t need to go anywhere near the relationship or marriage categories. And in your “About Me” paragraph simply put that you are looking for fun, distraction and nothing serious as your marriage recently ended and leave it at that. You say you don’t want to talk about it with a date, so don’t.  And once you go on dates, and they ask about your marriage (because they will), simply tell your date that at this point you don’t want to talk about the past or anything negative, and that you just want to get to know him and have fun. Most of the guys you will be going out with are also going to be divorced and probably don’t want to think about their ex-wives either!

Give it some time but in the meantime, allow yourself to discover the new, independent you! Good luck!

Dear Gems from Jen,

I am coming out of an almost 24 year marriage. My husband decided he did not want me/this marriage any longer, Ouch! Anyway, I am beginning to heal. I met a man through online dating and he has been in and out of relationships for awhile, nothing has stuck. We are keeping this at a friendship level so far. He knows I am not ready to give my heart and I want to be aware not to rebound. But, we went out the other night and I wanted to kiss him, but he gently told me no and I respected this. I have never had a real male friend. I am struggling with being attracted to him and wanting to kiss and hold and be held without ruining this friendship we are trying to build.  I am lonely and I am craving being held and kissed and wanted. I can’t tell if he is attracted to me this way or not. It feels like he is and he is respecting our friendship first unless I am totally hallucinating?!

What do I do?

Dear Friendship to More,

It sounds to me as if you might be a bit confused about what it is you are really looking for. On one hand you appear to be enjoying this friendship and on the other you seem to be craving physical intimacy. You are going to need to figure out what it is you truly want from this man.  Is it friendship or romance? Take some time to think about this question. Once you cross the friendship line there is no turning back. Take your time, there is no rush. It appears as if he is respectful of your friendship, so while you are thinking about what it is you really want, enjoy having a new friend!

Signed,

Gems from Jen

I have gotten several letters from JDaters inquiring about dating people who are divorced. What about the divorced daters out there? What are the guidelines, rules, and tips?

• Make sure you are over your ex before committing to a new relationship.  If you think about your ex and still feel emotion, whether it is anger or sadness, chances are you haven’t moved on completely.
• Remember, the person/people you are dating might have questions/concerns about the divorce.  Be honest, but only share when you feel ready.
• The person/people you are dating are not your ex.  Comparisons are unfair.
• If you have children, only introduce them to the new person when the two of you have entered into a committed relationship. Anything else can cause your children confusion, anger and hurt. Remember, you are entitled to have a life, but children should come first.
• Lastly, enjoy yourself. Divorce is serious business and can be very draining.  Give yourself permission to live life again.  Staring over can be an exciting journey. Time does heal the wounds and second chances in love are more common than most people really think!

Last week I met an old friend for bagels and coffee. She was divorced a few years ago and it was a very difficult time for not just her, but her family as well. Nonchalantly, between bites of my onion bagel with schmear, I asked her when she planned on dating again. Her expression told me the entire story. I was almost certain she was about to strangle me right there on the spot! She told me she was in no way ready to jump back into the dating pool. I then asked the question that almost assured my immediate demise. “When will you be ready?”

This conversation got me thinking about the term “ready.” What does being ready really mean? If we all waited until we were “ready” would we be on JDate? Are any of us really ready? What exactly are we getting ready for? Then the answer came to me. No one is ever ready, that’s life. So simple, yet it appears to be such a difficult concept. I called my girlfriend a few hours later and explained my epiphany to her. Needless to say she is now a JDate member. Is she ready? Am I ready? Are you ready? Life is about risks and all of us need to be proud of the fact that we have taken our dating into our own hands. It may not always end up the way we want, but you never know until you try.