Dear Jack and Maura,

I’m a 23-year-old straight male, and I’ve never been in a relationship. In fact, I’ve never even been on a second date before (and only a couple of first dates, for that matter). I’ve only ever kissed two girls, and that’s the extent of my sexual experience. I feel like I’ve missed out on so much over the years, and it’s made me wonder if there might be something horribly wrong with me. I’m seriously on the brink of giving up on dating (and everything that goes with it) altogether.

Moreover, I don’t think I’ve ever met anyone who is as much of a romantic “blank slate” as I am. Because I’ve never been in a relationship, I don’t have a reference point; I have no idea what kind of partner I’d be for a woman (whether I’d be clingy, whether I’d be open to the possibility of commitment, etc.). So not only do I think I’ve missed out on a wealth of experiences, but I’ve also missed out on the self-discovery (or whatever Disney cliché you want to use) that goes along with those experiences.

If you have any literature to recommend me, I’d greatly appreciate it.

Maura writes:

Dear Never Been in Love:

You haven’t missed out all! Very few people who are 23 truly know what they’d be like in a relationship. These are the years — your 20′s and 30′s — for figuring this stuff out. I know it’s hard to remember in our hyper-sexualized age, but you still have plenty of time for all sorts of experiences and self-discoveries — even if you may need to push yourself out of your comfort zone a bit to have them.

Read a book like “Jane Eyre,” and you’ll meet a main character a bit like yourself, even though she’s female. She lives a very lonely and solitary life — and surely has no idea what she‘d be like in a relationship — until she meets a true kindred spirit in her employer, a man named Edward Rochester. You might, however, feel more affinity with Margaret Schlegel, the heroine of “Howards End.” A thirty-something spinster, she’s pretty sure she won’t ever fall in love — until the day when an older male friend unexpectedly makes it clear that he’s deeply enamored of her by asking her to become his wife. His love for her is so strong that her own love grows out of it — and they go on to build a remarkable marriage.

But there are also male characters who think they’ll never find love, only to discover it unexpectedly — like Karim, a computer programmer who gets into a sweet relationship with his office mate, in the novel “Kapitoil,” by my friend Teddy Wayne. Or Raskolnikov, the murderer from “Crime and Punishment,” who is redeemed by the love of a good woman (who happens to be a prostitute). Although, come to think of it, maybe it’s not Raskolnikov who thought he’d never find love, but I who thought no one could ever love an over-educated, self-important jerk like him.

So please, Mr. Never Been, have faith! Remember how much opportunity and possibility there is out there — and how young you are. Life is yours for the living, friend.

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Dear Jack and Maura,

Two years ago I met a very sweet guy from out of town at a friend’s party. We kept in touch primarily via letters and saw each other once or twice a year. Since I met him I have been irrationally in love with him, but he always seemed a little cold to me (even though he supposedly cared for me). We didn’t declare our mutual love for one another (and he didn’t explain why he had been so paralyzed by his feelings for me) until after I had already moved a continent away. We’ve since decided to try being friends (leaving a romantic relationship to the unforeseeable), and I have a great new French boyfriend, but I don’t know how to let go of this guy back in the States. Help!

Jack writes:

My guess is that what you call “irrationally in love” is really just honest-to-goodness infatuation; you guys have only seen each other a few times, and each visit got to be a reunion. That doesn’t add up to the reality that long-term relationships have to go through.

A good literary example of this is Hans Castorp in Thomas Mann’s “The Magic Mountain.” He convinces himself he’s in love with Claudia Chauchat, another patient at the sanitarium he is staying in, but he’s barely exchanged introductions with her. Seeing how far he can go down the road of “love” without having real information is a warning to us all.

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Dear Maura and Jack,

My plight is simple: my beloved husband died in 2008 after a several-year struggle with cancer. While he was not my first husband or love, he was the best. Also the one I had a daughter with (she’s now away in college). I guess the woe is this: I’m 58, look OK, have a good job (though always precarious) and live in a metro-New York family town chock-full of younger Park Slope émigrés. I’m interested in finding someone, but know how hard it is, and I’m weary at the prospect. No one on Match.com who’s also interested in me seems interesting. I listen to live music, read and write a lot; I’m a little cynical; I’m a lot of fun. I do seek out books and movies that I can relate to, but somehow my life isn’t turning into “Shirley Valentine.”  I’m not Olive Kittredge, or some 70-plus widow either. Find my literature that balms my soul! Or gives me hope that even one such as I will serendipitously find love again.

Maura writes:

Dear Aging Cynically:

When I was 33, I had a tearful heart-to-heart with a friend of mine that ended with me saying, “I just feel too old to find love — like if my love juice hasn’t been activated yet by now, it’s probably expired.” He said, “Maura, sweetheart, you realize you’ve been saying that kind of thing since you were about 25, don’t you?” This is a long way of saying age might be a matter of perception more than anything else.

What’s more, I know of plenty of people who have found love unexpectedly much later in life — like my friends Donna and Ari, who found each other online when she was in her 50s and he was in his 60s. They’re like two newlyweds whenever I see them: always affectionate, holding hands, and kissing. If Match.com isn’t working out for you, why not try another site, like OkCupid? Or Alikewise, which caters especially to bibliophiles?

Or you could take a cue from “Love in the Time of Cholera.” The two main characters in that get together, finally, for the first time, when they are quite old … though the man, Florentino, has held a candle for the woman, Fermina, since they were kids. Do you happen to have any high school reunions coming up? Maybe you should go!

Another great — if far more bawdy — novel about love in older age is Philip Roth’s “Sabbath’s Theater.” The main character lives in a little Massachusetts town that might be a little like your New York town — and he and the town’s innkeeper fall into a passionate love affair when she’s in her late 50s, he in his 70s. It’s far from  a conventional relationship, but it brings them both new zest for life, inspiring in them deeper feelings (and lust) than they’d imagined they could feel. So perhaps it’s worth attending a few Chamber of Commerce meetings … or getting involved in local politics … or maybe just treating yourself to a drink at the little hotel in town, where that charming older bartender works.

Dear Maura and Jack,

I’ll keep this as short as I can, because the situation is quite simple really. After many years of keeping in touch across long distances (from occasional emails and phone calls to sleeping together if we happened to be in the same city), I finally live in the same city as a man I have been infatuated with, in love with and everything in between. Now that I’m here, he has become evasive, flaky and sometimes a flat-out jerk. I’m accustomed to being pursued and wooed and made a priority. Now I am bending over backward to try to see someone who changes plans, doesn’t make an effort to make time for me and doesn’t put any effort into our plans when we do get together. I have never been treated worse in my life. I have never been treated like this by a man — and yet I keep going back for more. I hate the way it makes me feel, but for some reason I can’t stop.