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Bintel Brief: Shoshanna Rikon on How To Help Singles — on the Sly

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.

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:

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

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:

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

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:

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Bintel Brief: Matchmaker, Matchmaker, Give Me Advice

Shoshanna Rikon is a Jewish cupid. The founder of Shoshanna’s Matches, 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, 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 Matches), she will be engaging in an equally venerable Jewish tradition: giving advice!

Do you have a question about love, life or loss? Do you have a dating dilemma or a Jewish conundrum? Could you use a little advice?

Send your questions for the Bintel Brief to bintelbrief@forward.com. Questions selected for publication are printed anonymously.

Check the Forward’s Web site Mondays in March for new installments of the Bintel Brief, featuring matchmaker Shoshanna Rikon.

To read previous installments of the Bintel Brief, click here. To read vintage Bintel Briefs and learn more about the column’s storied history, click here.

Bintel Brief: Lisa Loeb Says Honesty Is the Best Policy

Dear Lisa,

Not too long ago, a friend set me up on a blind date. Being a very shy person, I was naturally a bit nervous. But the guy was perfectly nice, and we had a pleasant conversation. There was no chemistry between us, however, which I recognized at the time, and so I planned to pursue it no further. Nevertheless, I left the evening somewhat encouraged because it was my first date in quite some time, and it wasn’t a painfully awkward experience — we managed to find things to talk about for a few hours and closed the evening on a friendly note. I told my friend that I appreciated the set-up.

Within the next day or so, I received an e-mail from the date. Though the e-mail was in theory a nice note — he was following up on some music suggestions I had mentioned — he also made a point to say that maybe we could hang out again sometime “as friends.” Now this, to me, was infuriating, like he was beating me to the rejection punch or something.

I had not contacted him, and so apparently his purpose in writing was to convey that he was not interested. Before receiving this e-mail, I felt there was no need for rejection until a second date was proposed. Was I wrong about that? Was there any way I could have saved face in my response to him and conveyed that the rejection was mutual without simply sounding like sour grapes?

Thanks for your thoughts on this matter.

BEATEN TO THE PUNCH

Lisa Loeb replies:

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