Dear Cary,
It was at the wedding of a friend who met her one and only on the Web that I decided to join millions of other young women and sign up for an online dating service. I've had some excellent dates and some really, really bad ones. The problem is, I spend so much time making sure they like me that I end up not liking them. In fact, I feel like I've flown through more men in the last few months than in my whole life. I'm still dateless and insecure. How is it possible to charm yourself out of a date?
Online and lonely
Dear Online and lonely,
Imagine yourself a wealthy ingénue, drenched in insouciance and engaged to a prince; imagine you've generously offered to baby-sit a lonely cousin, of whom you're fond but certainly not frightened. Consider carefully if it's worth answering his tiresome questions about your college, your family and the town you grew up in.
Maybe he won't like you, but what do you care? You're a wealthy and fabulous ingénue engaged to a prince. If he amuses you, later you two can get to know each other.
Or, if that's too metaphorical, you could just generally be yourself and stop trying to make these bozos like you. I mean, how intimidating can any guy be if you found him on an online dating service?
Dear Cary,
I am 21 and crazy in love with my boyfriend. He's sweet, handsome, considerate, fun to be with, great in bed and the kind of guy every woman wants. The only hitch is that he's not in love with me and we've been dating eight months already.
This is my first really serious boyfriend. My friends and family all think I should press the issue and demand to know why he doesn't say, "I love you."
He had a brutal breakup with his last girlfriend. They were going to get married and she dumped him. I am patient because I know it takes a while to open up to someone again. I even asked him how he felt and he said he "wasn't at that point" and just felt "empty inside" since his last relationship was so draining. I accepted that explanation.
That was five months ago. I don't want to be played with. I'm wondering if he likes the fact that someone is so in love with him and he doesn't have to reciprocate or get into a messy situation again. Is eight months long enough to know if you love somebody? Are my expectations too high?
M.E.
Dear M.E.,
At age 21, eight months seems like a long time, but in the scale of long-term relationships, it really isn't. If he's as great as you say, even though he's your first boyfriend, he could be the one you buy a dishwasher with. I'd just stick with him, be the best girlfriend you can be and don't set a deadline for his confession of undying love.
If you start placing demands on him, it could just remind him of how unworthy and mistrustful he felt after being dumped. Maybe he's waiting to see if you can be counted on. Try to quiet those anxious, insecure thoughts and just keep doing what you're doing. And find out if he knows how to load a dishwasher.
Dear Cary,
I'm 20 years old and have no romantic experience. I'm not just talking about sex, I'm talking about romantic kisses or even people who've liked me. I didn't think too much about it until the last few years, and then it turned into something where I was afraid to make myself known to a guy that I liked because I was afraid he wouldn't feel the same way. But I can't even bring myself to make the move -- you know what I mean? I don't want sex outside a relationship, but I want a kiss. That doesn't seem unreasonable, does it? What do I do?
Untouched
Dear Untouched,
You touched me with your letter. A kiss is not hard to get. The direct approach is best. You get with a guy you like who makes you feel warm, and when you're alone together you say, "Kiss me." That's all. If it doesn't work with him, try it on another guy, until you're thoroughly kissed.
Dear Cary,
I'm a 39-year-old civil rights attorney. I'm finally doing what I've always wanted to do -- at least professionally.
I grew up in and out of foster homes and institutions. I remember thinking as a kid that I could hardly wait to be in control of my own life, find the love, stability and family life that I'd always needed and wanted. I dropped out of school when I was 16 to help support my mother and siblings. It took 10 years to finally go back to school while I continued to work full-time. I earned my B.A. in two years and finished law school with honors.
Six years ago, I also ended a troubled five-year marriage because my wife was having an affair. She told me that she'd never really loved me anyway.
Here's the problem: Three years ago I started seeing someone whom I hoped to build a life with. She was brilliant, hardworking, funny -- a kind and gentle person. I fell deeply in love, but we agreed to take it slow and see how things developed. Unfortunately, after one year we broke up. She said she wasn't in love with me.
There aren't a lot of guys that'll admit to being badly hurt and disappointed, but I was. It's been two years since our breakup and I haven't been able to move on. I haven't dated or had sex since then either. I feel there's no love in my life; that there's never been any and might never be any. I feel burnt out, depleted, like I'm just going through the motions with no real purpose.
I also feel a profound sense of hopelessness and anger even though, at least professionally, I've been successful beyond my wildest dreams. I keep telling myself that I should just be grateful and satisfied with what I do have, which I know is a lot. And I am. For two years I've attempted to embrace my loneliness; come to terms with it. I've done that my whole life. But now, I'm just too tired. I'm losing my faith fast. It was this last go-around that broke me. The truth is, I simply can't get beyond this breakup. I've only felt that I'd been with the right woman, a truly compatible companion that one time. I know she's moved on with her life. I'm frustrated that I can't move on with mine.
Despondent in D.C.
Dear Despondent,
I don't tell many people this, but my advice to you is to find a good therapist and get some help moving through this. You're stuck. No shame in that. It happens.
You've tried it on your own and it hasn't worked. Think of it as calling a tow truck. You get stuck in the sand, you need some extra muscle to pull you out. It looks hopeless because you don't have the tools those guys have.
I had good luck with a therapist when I was in a similar situation: I could describe the problem, I knew I was stuck, but nothing I was doing was working; I just couldn't get through it on my own. He gave me just the right kind of shove and I came flying out of the hole. It was a huge moment. I'd wish it on anybody.
Good luck.
Dear Cary,
I am 25 years old and have been dating a 33-year-old for the last year. I love my boyfriend very much and feel comfortable thinking that we will get married.
I grew up overseas and often miss my old vagabond lifestyle. I hate my job and by luck was offered a home overseas where I know I will be able to find a better job. I told my boyfriend this and instantly saw that he was worried that I would leave him. Since he is older and has a very good job, I do not think that he would be willing to drop his life as fast as I would. What is holding me back is my love for my boyfriend.
The way I see it, if he does not have marriage plans with me in his future then I should not waste my time holding on to the unsuccessful life I have here. Although I love him very much, I often have this troubling feeling that I should do what is best for me while I am young. Things would be different if we were engaged. Then I would be working for our future because I would know that he wanted me in it.
Confused Vagabond
Dear Confused,
You don't sound confused at all. You're facing a conflict, but you don't sound confused about it. I think you're exactly right. You have to go. If he's got a great job and he can travel, he can visit you, and if nobody else comes along for either of you, you can still get married eventually, if that becomes the most important thing for both of you.
By the way: In case you're thinking of telling him that you'd stay if you were engaged, don't say it. Doing so would muddy the waters. If he asks you to marry him, consider it on its merits. But don't link it to this trip. If he does propose, you could always take this trip and still come back and marry him.
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