Dating 50 Year Old Man

[Hildegard Lobach]

Itwas in this state of contented disengagement that I met up with Jake on what would turn out to be one of our last nights together. We went to dinner with a friend of his from law school. The friend was cheerful, animated, solicitous: he seemed to detect the frigidness between Jake and me and did what he could to inject the evening with warmth. But I looked at the menu and saw the same preposterous prices. I listened to Jake hold forth on various topics with the same heedless, patronizing egoism. I looked out the window and envied the passersby. I knew it then: the experiment was over.

At the far end of the room, glass doors gave out onto a terrace. When I stepped into the fresh air I saw that the swiftly dropping temperature had kept everyone else inside: the lounge chairs were empty, the railing clear. I walked to the edge and laughed at myself for coming. I was several tax brackets beneath the next-poorest person here; I was an ex a few years away from being forgotten. But as I looked out at the city, twinkling beneath me like the disgorged contents of a great jewelry box, I felt a familiar, transcendent, dissociative sense of play. No one here except for Jake and the law school friend knew anything about me. I was as inconspicuously good-looking and responsibly dressed as anyone else. I could easily pass for an investment banker, a private equity associate, a trader: a presence that conveyed nothing so much as absence. The breeze quickened, my teeth chattered; I felt weightless and dizzy. Always playing, hiding, playing, hiding. After a few minutes I went back inside and made to leave.

But if your relationship with her is pretty good, do you feel challenged when it comes time to create and uphold reasonable boundaries? From where I am sitting, your 15-year-old is doing what she pleases and her boyfriend is telling you when he is going to have sex with her, and you are the only one feeling uneasy? (Sigh) Again, I am not criticizing you. It is easy to let rational boundaries slip away if upsetting emotions feel too big. But this scenario is an invitation to step into your role as a strong parent. That means voicing your concerns and having a conversation with your daughter about her life and your expectations.

Realistically, I am not overly concerned that he is 19 years old. A 19-year-old man may not be much different from a 16-, 17-, or 18-year-old boy, in terms of maturity. What I am concerned about is that your 15-year-old daughter is spending her time with a man who has an apartment and a full-time job. There are developmental milestones that he has had (graduating from high school) that your daughter may be missing out on if she is sitting at his place, watching TV and waiting for him to get home from work.

I was delighted, therefore, when I met Stephen Ellerker, a psychotherapist who at 73 had recently retrained to become a Kindling Dating coach and was teaching mid-life women like me how to date online. I met Ellerker when I had been interviewing him about an article about career change in your 70s. He had decided to train as an online dating coach when he had tried dating apps himself and had experienced the turmoil that they can create.

There is a lot of advice out there asking you to write a list of your ideal partner traits. Instead, Ellerker gets me to write a list of the feelings I want to feel. Safe (I need to trust the man), loved, sexy and entertained.

This works like a treat. On week two, I have three pre-date coffees in the diary. What do you wear? Where shall we meet? (Jeans and a cute top, an indie caf with good coffee in Newcastle.) Ridiculously nervous, I am exhausted before I even get there.

This is exactly the level of intimacy that is reserved for marriage only and that dating couples should make every effort to restrain until the appropriate time. Can this level of emotional intimacy happen between people who have been dating for a shorter amount of time? Of course. But the longer a couple dates, the harder it becomes to avoid it.

The longer the relationship, the higher the percentage. Where a relationship is shorter, accountability stronger, and the level of emotional intimacy more responsible, the level of physical temptation, and the likelihood of sin, goes down.

Scott Croft served for several years as chairman of the elders at Capitol Hill Baptist Church in Washington, D.C., where he wrote and taught the Friendship, Courtship & Marriage and Biblical Manhood & Womanhood CORE Seminars. Scott now lives in the Louisville, Ky., area with his wife, Rachel, and son, William, where he works as an attorney and serves as a member of Clifton Baptist Church.

Heroes come in all circumstances and ages. The prophet tells us, "Your old will have visions; your young will dream dreams." Elderly women in a retirement community in Mill Valley protested the war in Iraq on a busy thoroughfare with placards every Friday for years. A man I know of 22, halfway to a medical degree, is pursuing ballet dreams in New York City. Some people my age -- extreme middle-age -- train for marathons, or paddle down the Amazon, skydive, or adopt. They publish for the first time.

The thing was, I had just done something brave, which was to write a memoir with my son, tour the East Coast together, and appear on stages before hundreds of people at a time. But one dream coming true doesn't mean you give up on other lifelong dreams. You're not dream-greedy to want, say, a cool career and a mate. And having realized this one long-shot dream with my grown child gave me the confidence to try something even harder: to date.

I recoil even from the word "date," let alone the concept of possibly beginning a romantic relationship. Those woods are so spooky. I have an almost perfect life, even though I've been single since my last long-term boyfriend and I broke up four years ago. I really do, insofar as that is possible in this vale of tears -- a cherished family, a grandchild, church, career, sobriety, two dogs, daily hikes, naps, perfect friends. But sometimes I am lonely for a partner, a soul mate, a husband.

I had loved the sleeping alone part. I rarely missed sex: I had tiny boundary issues in all those years of drinking, and by my early 20s I had used up my lifelong allotment. I over-served myself. I do love what Wodehouse called the old oompus-boompus when it happens to be in progress, but wouldn't go out of my way. Additionally, I have spent approximately 1,736 hours of this one precious life waiting for the man to finish, and pretending that felt good. And I want a refund.

I am skittish about relationships, as most of the marriages I've seen up close have been ruinous for one or both parties. In four-fifths of them, the men want to have sex way more often than the women do. I would say almost none of the women would care if they ever got laid again, even when they are in good marriages. They do it because the man wants to. They do it because it makes the men like them more, and feel close for a while, but mostly women love it because they get to check it off their to-do lists. It means they get a pass for a week or two, or a month.

Yet union with a partner -- someone with whom to wake, whom you love, and talk with on and off all day, and sit with at dinner, and watch TV and movies, read together in bed, do hard tasks together, and to be loved by. That sounds really lovely.

I had experienced varying degrees of loneliness since my guy and I split up. After our breakup, I had just assumed there would be a bunch of kind, brilliant, liberal, funny guys my age to choose from. There always had been before. Surely my friends would set me up with their single friends, and besides, I am out in the public a lot doing events at bookstores and political gatherings, the ideal breeding ground for my type of guy. But I hadn't met anyone.

I went onto Match.com with a clear knowledge that relationships are not the answer to lifelong problems. They're hard, after the first trimester. People are damaged and needy and narcissistic. I sure am. Also, most men a single woman meets have been separated or divorced for about 20 minutes.

So the first morning, eight profiles of men varying in age from 54 to 63 arrived by email. Most seemed pretty normal, with college degrees, which I don't have, but certainly meant to; some attractive, mostly divorced but some like me, never married, some witty, some dull, sort of like real life.

Curiously, almost without exception, they were "spiritual but not religious." I thought for a while that this meant ecumenical, drawn to Rumi, Thomas Merton, Mary Oliver. But I have come to learn that this means they think of themselves as friendly. They are "glass half-full kind of people." That's very nice. They like to think that they are "closest to Buddhism," and "open to the magic that is all around us." They are "people-people." They are "open-minded and welcome all viewpoints." They are rarely seeking religious nuts like myself -- rather, they are seeking open, non-judgmental women. (The frequent reference to wanting a non-judgmental woman makes a girl worry: What if you're pretty non-judgmental, but then Larry Craig asks you out for coffee, or Buzz Bissinger, and little by little, more is revealed?) A strangely high number of them mention that they hope you've left your baggage at the airport -- because, I guess, they are all well! I love this so much.

Eight new guys arrived every day, along with a remnants section of men who lived pretty far away. Some of my eight guys were handsome, if you could believe their profiles, and in my case the profiles tended to be pretty legitimate. They mentioned that they drank moderately, or never, or socially (the most you can admit to. There is no way to check for "drinks alcoholically").

For my maiden voyage, I had coffee with an accomplished local man, who said his last girlfriend had been religious, a devout Jew, and this had driven him crazy. I said I was probably worse. We parted with a hug.

I selected a nice-looking Englishman with grown children for my second date. He said he had a good sense of humor, loved movies. He was, perhaps, the tiniest bit fat. I don't care much about weight, or hair loss. I emailed, and we arranged to meet at a Starbucks halfway between our homes, on a Sunday morning before my church.

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