Encountering Past Dates in the Wild: A Field Guide

by Caryn Alper under Date Night,JDate,Online Dating,Single Life

The world is split between two kinds of people: those who run toward an acquaintance at the grocery store, eager to say hello, and those who dart away and hide in the next aisle in an effort to avoid forced small talk.  Which kind of person are you?

Do you fall into the same camp if the acquaintance is someone you previously dated? What if you recognize someone with whom you’ve previously changed messages, but you never met in person? What if the other person doesn’t recognize you? What’s the protocol here?

Relax, dear readers, I’ve got the rules below.

First, as a natural hider, let me say that avoidance is always an acceptable option.  On days where I just don’t feel like talking to someone, or I’m in work-out clothes with post-gym hair, or whatever, I’ve been known to feign interest in the nutrition facts of Worchester sauce until the perceived social threat has passed.  However, once you commit to the avoidance tactic, what would have been a 10-minute run to the store can easily turn into a tactical strategy of hard-core hide and seek.  Be forewarned.

But once eye contact has been established with the acquaintance, things get a little trickier.  Proceed as indicated below:

If you recognize someone who…

  • Is on JDate and you might be interested: Smile and make eye contact
  • Is on JDate and you are probably not interested: Avoid or smile weakly
  • You recently exchanged messages with: Smile and make eye contact
  • You exchanged messages over 6 months ago but never met: Avoid or smile, depending on whether you are still interested
  • You went out with once or twice: Smile
  • You went out with on the worst date of your life: Avoid — or, if you’re in a movie, make a loud scene resulting in the destruction of a pyramid of produce, causing innocent bystanders to start tripping over oranges
  • You dated for a few months: Smile and wave politely, depending on how things ended
  • You dated for a substantial amount of time: This really depends on the nature of your relationships, but given its length, you will know what feels most comfortable
  • Is a random, cute stranger: Smile! And ask for a food recommendation  – why not?

If you’re ever unsure whether to approach someone whose relationship isn’t listed above, come find me for consultation – I’ll be the one hiding behind giant sunglasses pretending to inspect the melons really closely.

Friends with Ex-Boyfriends

by Tamar Caspi under Date Night,Online Dating,Relationships,Single Life

Hi Tamar,

I was with my ex-boyfriend for four years. Since breaking up, we’ve been able to remain good friends. In fact, I’m still friends with most of my exes and I thought guys would see this as a good thing – that I’m known as a good person and clearly don’t attract drama. But, when I mentioned hanging out with an ex to my most recent dates, the guys were not cool with it at all. One even straight-up asked if I was still having sex with an ex! (We are not.) Why do the guys have a problem with this? Is it their problem or mine?

-Friendly Femme


Dear Friendly Femme

Theoretically, a man who is secure with himself, and your relationship with him, shouldn’t have a problem with you having a friendship with another man. It does become more complicated when you had a romantic relationship with that man in the past. Most men assume that a “guy-friend” – particularly one you had sex with in the past – is really only hanging around for (more) eventual sex. Being around an ex can make a new guy feel intimidated.

My advice is this: in order to find the man you want to spend the rest of your life with, you may need to put some distance between yourself and your exes. I personally don’t see a reason to be friends with every single one, but I do understand that you spent a good chunk of your life with someone and don’t want to lose that piece of your life. You need to ask yourself what an ex – or any friend for that matter – is contributing to your life? If you haven’t realized this yet, you will eventually: friendships are about quality, not quantity.

I suggest not mentioning your guy friends on a date, or the fact that those guy friends are exes. If things get serious and you begin introducing your new beau to your friends, then you will need to give a history ahead of time. But, you may also find you no longer want to be friends with an ex as things get more serious with someone else. Certain people from your past should stay in your past — even if the break-up was cordial and you get along now.

Discussing Your Dating Past

by Tamar Caspi under Relationships

On a first or second date one will typically be asked when was the last time you were in a relationship. There are really only a few answers to give and ways to give said answers.

–if you got your heartbroken recently, then simply say “I had a not so fun break-up a few months ago but I learned so much from it and am ready to have fun again.”

–if you just got out of a long relationship, then reply “I was with someone for awhile but in the end we realized we wanted different things.”

–if you haven’t been in a relationship in more than a year, then say “it’s been a while and I’ve been meeting lots of nice people but no one that I’ve wanted to take it to the next level with.”

Leave it at one line, using some kind of variation of the above depending upon your circumstance. If and when this date becomes a relationship then you can exchange stories and delve deeper, but for the first few dates it’s not worth it. A longer explanation will only put a damper on the date. If you have to ask the question then at least preempt it with “I don’t want to know the details right now, but I was wondering when the last relationship you were in was?” and if you’re asked the question first then you will need to ask it in return whether you want to or not because it’s the polite thing to do. Then move on to another topic.

Q&A — My Past Relationships

by Tamar Caspi under Relationships

How do you answer JDate’s questions without sounding repetitive or cheesy or fake or boring? Let me help you craft personal and inticing answers to both the basic and intimate questions.

“My Past Relationships”

There’s no need to discuss why you were just dumped or why you broke up with your last significant other. Don’t get into the details here of what went wrong, rather talk about what you learned from the demise. This section’s answer shouldn’t be too lengthy, if you find that you’re writing a novel then take that to a journal and leave just the life lessons in your response.

Some examples to use:

I learned what kind of boy/girlfriend I want to be and what kind of girl/boyfriend I need and want

I learned not to sweat the small stuff

I learned that I need affection and that I need someone who enjoys affection in return

I learned how to communicate more effectively

I learned that it’s boring to always agree, but that we need to disagree in a healthy way

I learned not to let things fester but to calmly address issues as they arise

I learned that mutual respect is just as important as mutual attraction


by Tamar Caspi under Relationships

Now that we’ve accomplished that (almost) everyone on JDate has already had sex, let’s talk about sex baby. You can probably make assumptions about the amount of sexual experience someone has had, but you know what they say what happens when you assume – you make an “ass” out of “u” and “me.” Just because someone has all the right moves and knows what you like doesn’t mean that he or she was promiscuous before meeting you. Just because someone is an awful kisser and an awkward lover doesn’t mean that he or she was a prude before meeting you either. Don’t worry about what your partner did or didn’t do B.Y. (before you), concentrate on your chemistry together and on the experiences you will create together. If you spend your time pondering too much about where your date has been B.Y., it means you’re not spending enough time wondering about where the date could lead.

B.Y. is none of your business. It does not matter. Accept your date for who they are and move on. If you can’t, then that person isn’t right for you. You need to find that someone who you can accept without doubt because you want to be with them more than you want to know about their past.

The Past Has Passed

by Tamar Caspi under JDate,Online Dating,Relationships

JDate asks you a question: what have you learned from your past relationships, or, simply “My Past Relationships”? It’s a tricky question but you’ve got to answer it. For the most part, the Jewish community is small, so even though you may not personally know a JDater, you may know who they’re talking about in that paragraph.

Stating that you now know that you don’t want someone who is ‘a spoiled, trust fund brat’ or a ‘pompous, egomaniac, even if he is a doctor’ will actually make you look bad, not better. You’re talking badly about an ex rather than showing what you learned about yourself. Not only does it make you look immature, but it’s gossip and it’s ugly. Use this opportunity to talk about how you have grown and the person you want to be instead.