Where to start?

I’d just gotten out of a bad six-year relationship with a non-Jewish guy. I was about to move to Boston for grad school, so I thought why not hop on a dating site and find an NJB? You know, to have him before I even moved there. Good life planning!

Well. A guy checked out my profile, so I looked at his. Within minutes, “39 year-old” David (actual schmuck’s name, he deserves no protection) messaged me. We chatted for hours. He was a successful doctor, tech entrepreneur, 11 years older than me, never married, no kids. Excellent. We chat nonstop via text and phone for weeks. In the course of our chatting, he casually mentions he wouldn’t be answering texts on Saturday because he’s Orthodox. Fine. I respect that. Everyone has their thing. Mine is designer purses and air conditioning. His is Shabbos. Within a few weeks, I find myself up there for accepted student weekend and to get an apartment. We planned on meeting up while I was there.

Before my trip to Boston, he asks me to go to the mikveh, something I’ve never done before. I don’t really understand why, but I go anyway. He thinks it’s “super hot” I went for him. As I pack the evening before I leave for Boston, we’re chatting and I make some sort of age joke. “I’m older than you know,” he says. I knew it! I could tell by his pictures that he wasn’t 39, but I couldn’t tell exactly how old he was. But I move on. When we meet for a Passover wine tasting in Boston, I immediately know he’s in his 50s, but he doesn’t admit to being 58 until his birthday a few months later.

After we wine taste, he wants a drink at my hotel bar. I don’t see why not, so we go. It becomes clear to me that he wants sex. I’m confused but also having that fat girl moment where a man shows interest in me and I can’t say no or else he won’t like me anymore. I’m a good Reform Jewish girl, but everything I know about Orthodoxy is so opposite of what’s happening, not that I particularly care. It’s another huge red flag I ignore because he’s my NJB future. He even called himself my boyfriend in texts before.

In my hotel room, he tells me we can’t use condoms because it’s against halacha, traditional Jewish law. Ummm, is it any more of a rule violation than what’s about to happen? After, he holds me in his arms as he tells me he has to do his younger daughter’s taxes; his ex-wife does it for their eldest daughter. I’m too — something — to be mad. He has to shower because he can’t put on his tzitzit if he’s “unclean.” My vagina made him dirty. Fucking rude.

I don’t see him again until I move to Boston a few months later, but we talk almost every day. He texts me before he lights candles on Friday night and after he sees three stars in the sky on Saturday night. I know my pushing-60 NJB is a loaded liar. I ignore it all. I ignore the pattern of texting all the time, only to have sex in my apartment and to only go out together (rarely) in my neighborhood, never his.

He lets it “accidentally” slip that I can’t go to some Jewish events for young Jewish professionals because he’ll be there. That’s bullshit and I tell him so. I also remind him that while he’s a professional, he’s not “young.” He laughs. He knows, but he is a huge donor to this particular organization so he goes to all of their events (probably to find his next inappropriately aged lay). For Purim, he reads the whole Megillah twice at their annual party. I can’t go, he says, because they’d see it on my face, the way that I look at him, that we’re not following the rules. I remind him that they’re not my rules and my rabbi doesn’t particularly care if and when I have sex or hold someone’s hand. My rabbi doesn’t count, he says, because she’s a woman and women can’t be rabbis. I remind him women, myself and my rabbi included, are closer to God than he’ll ever be. He’s annoyed by my Jewish feminism and understanding of Torah.

This goes on for three years. I don’t know his friends or family. He doesn’t know mine, though he’s willing to meet them, in theory. I present my graduate practicum poster and he shows up to support me. We walk back to my place. We can’t hold hands, that’s not frum, like him. When I need him, he isn’t there. When I ask for help, he can’t give it. When I ask why we can’t go out in the very Jewish suburb where he lives, he mumbles something about my neighborhood having better food and wine. Three years.

I graduate, get a job, buy a car, and move to the Jewish suburbs. He won’t come over. For months. Yet, he texts me all the time. I realize that, over the past three years, he’s still been on JDate, JSwipe, OKC, and Tinder. He always joked he was my perfect Jewish boyfriend. He talked about the babies of his I’d have. We agreed on names, their education. But it’s been months since I’ve seen him. I know I’m not really his girlfriend. I never was. I know he doesn’t love me. I know he’s just making my pre-existing daddy issues worse.

But I keep texting him. Maybe, if I lose weight, if I get prettier by some miracle of God. If I become Jewish enough. Dayenu?

We both wind up going to Israel and our trips overlap by about 36 hours. I’m on Birthright and he’s there for Sukkot. I tell him for weeks where I’m staying in Jerusalem, the dates of my extended trip. He calls and asks if he can come over. I’ve had such an incredible journey so far that I say no, he can’t come over for sex in Israel if he can’t come over at home. Not in the Old City. I won’t do it anymore. He tries to laugh it off, says I’m just being emotional; “Israel can do that to you.”

I go home and cry for all 13 hours of my flight. Just a week before, at the Western Wall for the first time, I ask, I pray, I beg God to tell me what to do about David. I know we’ll never be married. He’ll never give me the Jewish babies I want, the ones he has promised me for three years.

When he’s back in the US, I text to welcome him home and ask if his flight was okay. He replies that he’s in a relationship now and we can’t talk anymore. I wish him the future with her that he promised me.

I never believed we were actually in a relationship, and I was right. I still see him checking my profile now, almost a year later. We haven’t spoken, though I have a lot to say. For three years I was the secret play-thing of a man who lived at least two lives. The frum philanthropist in the Jewish suburbs, and the “off the derech” doctor with me.

I won’t lie, I’m still heartbroken, even though I know what I should be is mad.

What a fucking schmuck.

what a schmuck