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Dating Column for The Jewish Forward Newspaper

Shoshanna Rikon is a Jewish cupid. The founder of Shoshanna’s Matchmaking Service, Rikon works to create love connections for Jewish singles in the New York tri-state area. Her work as an old-fashioned matchmaker in the town that gave the world “Sex and the City” has caught the attention of media outlets ranging from The New York Times to the Forward and landed her on “Dr. Phil” and VH1.

For the month of March 2008, Rikon will be moonlighting as Forward’s guest Bintel Brief columnist. While she won’t be making matches (for that, you’d have to join Shoshanna’s Matchmaking Service), she will be engaging in an equally venerable Jewish tradition: giving advice!

Shoshanna Rikon on How To Help Singles — on the Sly

Posted by Shoshanna Rikon, March 24, 2008, 9:54 pm

Shoshanna Rikon

Dear Shoshanna,

I’m a rabbi, and I’m working with my local Jewish community center to form a singles group. There are a lot of singles in our community, and we’re concerned about the escalating intermarriage that goes on.

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We want to develop some programming to attract Jewish singles so that they can meet each other and socialize — and maybe, from there, relationships will form. We’re thinking of targeting those between the ages of 40 and 60, people who have never been married and those who have been married but do not have a partner anymore.

It’s very difficult for singles. Many of them are dissatisfied with the singles events and groups that currently exist in our area. I think that many of the people who go to such events feel intimidated. If they’ve gone once, they come back a year later and they see the same people. They basically receive a lot of negativism and are turned off.

We want to create a more attractive environment. Do you have any ideas how we can accomplish this? Your guidance would be greatly appreciated.

ASPIRING CUPID

Shoshanna Rikon replies:

Singles events and mixers sometimes can be more harmful to a single or newly single person’s ego than not meeting anyone new at all. Unfortunately, many people who patronize these events are socially awkward. They are men and woman who are not able to meet singles through conventional, modern-day introductions (i.e. through co-workers, friends and family; in bars, through on-line dating sites or using personal ads). Many of these singles events end up seeming like old-school junior high dances where the men are all gathered around the refreshment stand while the woman sit with the friends they came with and either hope that a gentleman talks to them or, more commonly, hope that no one who knows them sees them there at all.

I have attended a singles event or two in my day and, unfortunately, I experienced the same results. It is sad, because many of these people would like to find a meaningful relationship but do not have the tools or confidence to approach a stranger and introduce themselves. Many people are intimidated by being single and are fearful of being rejected, so they sit by themselves and meet no one at all. Other people who have attended these singles events get disenchanted quickly if they do not see people they are interested in. (Meaning: They do not find the gathering of people to be attractive and leave in a hurry.) That is the exact reason why I created my company, Shoshanna’s Matchmaking Service. I realized that some people need another set of eyes and ears looking out for their best interests, and that’s where my business model began.

I do understand that not everyone is open-minded or ready to outsource their pursuit of the perfect mate to someone else, so here is my suggestion to help out those who are single in your community: Instead of a “singles event,” how about organizing a fund-raiser or a community outreach program where singles can sign up and use their time to give back to the community, as well as meet new people with similar interests. Volunteering one’s time is not only good for the community; it also enables a person to feel better about his or her own self-worth. Every day many single people join organizations like Big Brothers/Big Sisters or sign up for charitable events like the Avon Walk (proceeds going to treatment and cure for breast cancer).

Before I was a matchmaker — which seems like a lifetime ago — I worked in human resources. My first boss after college was a gentleman who had a Rolodex of the “who’s who” of Manhattan’s social, political and financial circles. So it came as a complete shock to me that he had met his second wife at a political fund-raiser. At first, I was perplexed, because this is a man who could be introduced to everyone and anyone. As I got to know him and his wife, I realized that it was their common interests that solidified them as a couple, and that if it weren’t for their love of the Democratic Party, they would never have met and married.

My advice to you, rabbi, is to do something for your entire community and organize a fund-raiser or an event to sponsor a charitable cause that your congregation and community can get behind. Give singles an opportunity to meet people who share their interests in a more natural environment than the pressure-cooker of a singles mixer.

Shoshanna Rikon is the founder of Shoshanna’s Matchmaking Service, which serves Jewish singles in the New York tri-state area.

 


Shoshanna Rikon Says Not All Skeletons Should Be Left in the Closet

Posted by Shoshanna Rikon, March 17, 2008, 3:18 pm

Shoshanna Rikon

Dear Shoshanna,

My boyfriend rarely asks me anything about past affairs, which is fine by me. But I’m wondering if I’m obliged to divulge some facts nonetheless.

The problem is that one of our best couple friends includes a man with whom I had a brief affair several years ago — well before I met my boyfriend. This other friend and I remain close, but I’m no longer interested in him sexually or romantically in the least, and so I hesitate to tell my boyfriend about it. I don’t want the friendship made awkward by the past and, more importantly, I don’t want to hurt my boyfriend needlessly. I get the impression that the girlfriend of my old fling also knows nothing of our affair.

Should I tell my boyfriend about my history with this friend? Or is it better to keep quiet about it?

MUM’S THE WORD?

Shoshanna Rikon replies:

Most men do not want to hear about a woman’s past relationships. Men don’t need, nor do they want, to be reminded that they were not your first conquest. Discussing every past relationship you had with your present mate is counterproductive and could potentially damage your relationship.

This, however, is a different case. My philosophy is that nothing beats honesty! Explaining to your boyfriend that the gentleman the two of you have befriended was once a lover of yours should not bruise his ego too much — especially if it was a lifetime ago. That is also assuming that you are dating a strong man who is confident and comfortable in his own skin.

Even if your boyfriend is angered or embarrassed at first, he will eventually come to his senses and realize that it is your love, trust and devotion that led you to bare your soul and be honest with him. In my opinion, this can only solidify the relationship and make your bond stronger. If you choose the other path, you run the risk of your former flame admitting the truth to his girlfriend or, worse, to your boyfriend. Then you are caught and might be viewed as being sneaky, which is never a good thing and can possibly destroy the relationship you have been building.

If you truly love someone, then you need to be honest! No, that does not mean that you need to bring out all the skeletons in your closet — just the ones that could affect your relationship. Believe me, in the end he will love and respect you more for being honest than for trying to spare his feelings.

Shoshanna Rikon is the founder of Shoshanna’s Matchmaking Service, which serves Jewish singles in the New York tri-state area.

 


Shoshanna Rikon Says ‘Concentrate on What Is in Front of You’

Posted by Shoshanna Rikon, March 10, 2008, 1:13 pm

Shoshanna Rikon

Dear Shoshanna,

I recently broke up with my girlfriend of many years, which was a tough, but correct, decision. While we were dating, I considered breaking up with her over a woman for whom I can only describe my feelings as intoxicating (the reason why I didn’t was because I was going to move away shortly). Then, the other night, I randomly ran into this woman and, though I thought the feelings were long gone, they reappeared almost instantly. I didn’t make a move that night, but I believe based on her body language and our conversation that there are at the very least residual feelings on her part as well. My problem? At the night’s end, she told me two things: 1) I have a boyfriend, and 2) don’t be a stranger. Is she sending me deliberately mixed messages, or am I simply misreading things entirely?

SIGNALS CROSSED

Shoshanna Rikon replies:

Before I answer your question regarding this mystery woman who you feel might be sending you “mixed signals,” I want to address your comments about your former girlfriend. Not every relationship turns into marriage. We do need to go through the dating process to figure out whether or not we have found someone to share our life with. You recently broke up with your girlfriend whom you dated for “many years,” yet you openly admit to having feelings for another during the time of your relationship. Always try to concentrate on what is in front of you!

Now, to answer your question involving this “intoxicating” woman: Maybe it is mixed signals, but it is more than likely that she is just not interested in you. You recently tried to rekindle the flame with her, yet you never actually had any type of relationship. You have probably just created this illusion for yourself of how lovely life with her is. However, the mutual attraction has not actually existed. Does she have a boyfriend — or is she merely saying it to avoid any more awkward evenings with you? When a woman says a vague general tagline, she is simply being coy and pacifying you to keep the environment comfortable. If a woman wanted to see you again, she would jump at the opportunity to and have her agenda readily available. She is likely not interested in you.

Shoshanna Rikon is the founder of Shoshanna’s Matchmaking Service, which serves Jewish singles in the New York tri-state area.

 


Matchmaker, Matchmaker...
Hoping To Stave Off the Valentine's Day Blues, the Hapless Jewish Writer Seeks Professional Help
By Max Gross

February 11, 2005

Valentine's Day can summon terrible sadness in Hapless Jews. Last Valentine's Day, the Hapless Jewish Writer spent the day despairing over his ex.

The Hapless Jewish Writer's girlfriend ended their relationship at an Indian restaurant December 7 — a date that will live in infamy.

"I love you," his treacherous blonde-haired vixen declared. "I'm just not in love with you."

Now that's cold.

In fact they were the exact same words that Elizabeth Shue said to Woody Allen in "Deconstructing Harry" — a film that the HJW and his girlfriend had watched a few weeks earlier.

"She couldn't come up with something more original?" the HJW thought as he stared angrily at his linen napkin.

The HJW and his girl would reconcile briefly, but it was not to last. And he fell into an extreme depression. When he stayed home he sobbed into his pillow. When he left his apartment he drank himself to drunkenness, passing out on friends' floors. He would hold the Barneys necktie that she gave him for his birthday in his hands as if it were a relic from the Second Temple. He begged friends for advice on how to win her back; they told him to move on. His mother recommended that he see a psychiatrist.

And as often happens during the great calamities of his life, the HJW felt the tug of his ancestry and civilization. In moments of despair the HJW fantasized about returning to the religious, shtetly life that his great-grandparents abandoned when they landed on these shores.

So it almost seemed like providence when, in the middle of his crisis, a PR agent contacted the HJW and suggested that he write a story about Shoshanna, the Jewish matchmaker — and use himself as a test case for her matchmaking gifts.

"Sure," the HJW said. Maybe a good Old World Jewish match was all he really needed.

Known professionally as Shoshanna, Shoshanna Rikon works out of a small office on New York City's Fifth Avenue, which she shares with her assistant, Melissa. And if the HJW was expecting a bent-over little Jewish woman with a kerchief wrapped around her hair, he was in for a surprise. Shoshanna is a tall, brunet Staten Island native with a brusque, no-nonsense New York manner.

Many of the 30-somethings and 40-somethings who visit Shoshanna are sent there by their mothers. "It's awkward to join the service," Shoshanna told the HJW. In an uncompromising quest for grandchildren, mothers nudge their adult children along. ("You know," one of the mothers told Shoshanna, "I'm [your] only competition.")

"So what are you looking for?" Shoshanna asked the HJW.

"Someone nice," he said.

"What about looks?" Shoshanna asked.

"Well, it's important."

"Is weight important?"

"What do you mean?"

"Well," Shoshanna said, "we have very pretty girls who are heavy. I mean, not so heavy that you can't get your arms around them, but..."

He would prefer someone who is not fat, the HJW said. (He felt shallow and guilty for the rest of the day. Oh, how shallow and empty to... whatever.)

The HJW was sent home and told that Melissa would call him with possible dates.

Melissa called him a few days later and swore up and down that number one was a looker. She worked at a magazine, and Melissa was confident that the two of them would hit it off. ("Melissa does that [with] everybody," Shoshanna said later. "She sees the good in them... I'm the one who's the honest one. I say, ‘No! That guy's dead ugly.'")

The HJW and number one made a date to meet each other at a coffee shop near the HJW's office, but she called to cancel. She also told him that she was going to be out of town — recovering from an operation — for the next month.

It was too elaborate an excuse to be a lie, the HJW reasoned. She couldn't have heard about his past already...

But number one and the HJW were not destined to cross paths. A month later, the HJW left a message on her machine, wishing her well and hoping that she had recovered. But number one phoned Melissa and said that she thought the HJW sounded too young. (She was a year older.)

On to number two.

It was a pleasant enough date. The two met at a bar on the Upper West Side near number two's house, ordered several weird, fruity drinks and spent the next two hours talking about restaurants and a few small towns in Israel that they both knew. The HJW left the date confident enough to ask out number two again. She accepted.

A day or two later, the HJW found a message on his machine saying that upon reflection, she, too, thought he was too young. "I hope we can be friends — if you want," number two said, and her voice trailed off.

The HJW had very little in common with number three. They met for drinks at the Algonquin Hotel, and the HJW found himself struggling to find things to talk about. He was happy to hear that she, too, disliked the movie "The Matrix," but that was the high point of the conversation.

Number four and the HJW played phone tag on their answering machines for about a week. After the message swapping had gone on for a few days, the HJW came home and discovered a message from Melissa.

"I don't mean to sound like a Jewish mother, here," Melissa began — always the sign of a bad conversation.

During the course of the rest of her message, the HJW loosened his tie, removed his shirt, washed his face and changed his clothes. When he came back to his machine, Melissa was still speaking.

"She's really a great girl. I really think you'll hit it off."

Translation: Don't blow it by not calling her back.

Finally the HJW and number four met, and had a pleasant enough date. Later, the HJW was more than a little surprised to hear number four's analysis:

1) The HJW was dorky looking. (The HJW wore glasses.)

2) His hair was too bushy. (The HJW always wore a red Jewfro with pride.)

3) He was a little out of shape. (That hurt. He had lost 20 pounds after his girlfriend dumped him, and he had kept most of it off. Besides, this chick wasn't exactly Gwyneth Paltrow.)

The HJW went back to Shoshanna's office, and Shoshanna shook her head at the women who rejected him. "What I personally like about you is you're willing to go on the second date," Shoshanna said. "More people should be like you, [HJW]."

Shoshanna and the HJW spent an hour or two reminiscing about the weird types who had floated in and out of her office throughout the years. There was a fellow who had come in with stains on his shirt and with an overpowering body odor (Shoshanna turned him away, but not before making some helpful hygienic suggestions), and a number of non-Jewish women who came in looking for Jewish husbands.

Shoshanna and the HJW left the office and went to a bar for one of Shoshanna's matchmaking parties, which she throws every few months.

The HJW milled about the party for roughly an hour, martini in hand, when, on his way to the bathroom, he bumped into a small, munchkinlike woman with blond hair.

Shoshanna leaned over and whispered in his ear, "Talk to her!"

The HJW and his new friend struck up a conversation. And before he left the party he got her number. They started going out.

After his initial glow of enthusiasm died down, however, the HJW remembered all the claustrophobic feelings of an attached man. Number five was warm, kind and intelligent, and after a couple of months the HJW felt very afraid. He would be nervous every time the phone rang. He began thinking up excuses to get himself out of dates. He began acting like, for lack of a better word, a schmuck.

He gathered up his courage and broke up with her.

Like clockwork, Melissa called him a week or two later with another match. But by that time, the HJW was a little tired of matchmaking. He met a gorgeous blond shiksa at a party; the next week they canoodled at a bar, and they have been going out ever since.

The HJW realized that there was more than a hint of drama in his desire to go Old World Jewish shtetly. He's happy dating his lovely shiksa. But he doesn't have bad things to say about matchmakers — in the ruthlessness of the New York dating world, we Hapless Jews should try it all.

Max Gross is a writer living in New York, and a frequent contributor to the Forward.