Only relatively recently have I considered dating. I finally have a great job where I can support myself, and save up enough to support my sister in the future because it doesn’t seem like she will ever be able to take care of herself. I’ve gotten counseling and support from close friends and family, and am in generally a much better place than even just three years ago. Unfortunately, because of my past and choosing to be the complete opposite of my father, I have turned into the stereotypical “nice guy” who pretty much every girl says she wants, but ends up never going out with. So forget the bar scene entirely; I chose to start dating via Match.com.
So far, in the seven months I’ve been on the site, I’ve gone on three dates. As far as I’m concerned, that’s as big an achievement for me as flying to the moon was for the human race. My problem is that I was never comfortable on the dates because of this giant 800 lb. gorilla in the room. And of course it showed; I asked the women out for a second date, and all three times I got “You’re a nice guy and all, but…” And this is where I’m looking for your help; how in the world can I convey to the women on the site that I’m really not like most other guys there? Do I just tell the truth about my life story from the start? I fear that if I say that I’ve never kissed a woman, they’re all going to click “back” on the browser in a millisecond and never give me a chance. How do I write my profile to say that I’m probably going to be one of the nicest, and shyest, guys these women will ever meet, but without falling into the trap of being the “boring, unchallenging, nice guy”? What sort of things should I write, and how should I write them? How should I write an opening email to a woman I’m interested in on the site? I know it’s a lot of questions to ask, and I have hundreds more, but I really have zero experience when it comes to anything dating-related, so any advice you’d be willing to give would be fantastic. — Hopefully not 40-Year Old Virgin
It’s wonderful that you have risen above your messy childhood and are making something of yourself. It shows amazing character that you are actively planning for the long-term care of your sister. And it’s great that, despite your insecurities and lack of experience, you’re giving a real go at the whole dating thing. But, dude, if you’re going to be successful and find a good match for yourself, you’ve got to change your attitude — and fast!
First of all, it’s a myth that women aren’t into “nice guys.” As someone who married a “nice guy,” I PROMISE you that for many of us, there’s nothing hotter than a guy who’s got our back and makes us feel valued and respected. There are two secrets here to finding your match. First, you need to look for women with self-respect — they’re going to be the ones who are over the stupid game-playing and all the drama that comes from dating guys who treat them like shit. Second, you need to believe in yourself — believe you are and have something of value to offer the ladies. And you need to lead with that. Always, always, always lead with your strengths, not your flaws.
So, let’s start with that, shall we? Instead of telling women in your profile or on a first date that you’re inexperienced and you’ve never kissed a woman and your super shy and blah, blah, blah, focus on the stuff that you’re confident about — that you have a great job you love, and a solid group of friends, and you’re the kind of person people can turn to and depend on. Make a list of things you love about yourself and lead with all that. Better yet, hire me and I’ll help you compose your dating profile. We’ll get rid of all the stupid negatives you seem fixated on and package you as the amazing catch you are.
When it comes to first dates — or second or third dates — there is absolutely no reason you have to tell a woman you’ve never kissed anyone. I would NOT bring this up. I wouldn’t even think about it when you’re on a date. Instead, focus on getting to know her, asking her questions about herself, and sharing personal stories that give her a sense of who you are and what you’re looking for. Great first date topics include: what you like to do for fun; movies, books, and music you love; places you’ve visited; where you grew up and went to school; and goals you have for the future (“I’d love to start my own business in a few years,” or “I hope to run a half-marathon in six months.”). Stay away from awkward or painful topics until you are much more comfortable with each other: your alcoholic father and abusive childhood; your relationship and sexual inexperience; that time your sister walked in on your jerking off. Keep things light and neutral.
Dating isn’t rocket science. There’s really not a steep learning curve here. If you’re engaged in the world around you and you’ve managed to make it to 26 without being a total hermit, you already have dating skills and you don’t even know it. Dating is simply about getting to know other people and seeing if you have enough chemistry to invest time in each other’s company. Honestly, that’s all it is. You don’t have to have kissed a million girls to be able to do that. You’ve been doing it all your life. It’s how you make friends. It’s how you land jobs. The only difference with dating is that eventually you have to decide if you like each other enough and have enough chemistry to be physically intimate. You can decide that on date #1, or you can take your time. There are no rules. It’s about how you both feel. And if you want to kiss a girl and you think you’re getting some clues from her that she’d like you to, too — she’s been playing with her hair, making lots of eye contact, licking her lips, smiling a lot, and gently touching you when she’s talking — go for it! Lean in and give her a little peck. If she leans into you, take it a little deeper, pull her a little closer. If she’s resistant or turns away, no harm. Maybe you just read her signals wrong. Maybe she’s interested in you but not ready to kiss yet. Or maybe she’s just not feeling it. Whatever; who cares! You won’t have been the first person in the world to not be kissed back. It happens ALL THE TIME, and it’s not a big deal. It doesn’t mean you’re doomed to be single or that you’re not challenging enough or whatever other bullshit you’ve convinced yourself has made you undesirable. It simply means that this one woman in this particular moment wasn’t feeling exactly what you felt. So, move on. See if she wants to go out again and try it one more time. If not, tell her it was nice to meet her, wish her well and move on to the next woman. Because there will be a next woman. And as long as you keep trying and keep being yourself and having confidence that you are and have something of value to offer a woman, you’re going to find someone who wants to be with you. It will happen. There are women who want what you have. You just need to be clear about what it is you’re offering and quit focusing on what it is you aren’t. Capiche? Good.
*If you have a relationship/dating question I can help answer, send me your letters at email@example.com and be sure to follow me on Twitter.