I’m 32 and have never had a girlfriend. I’m not a touchy-feely person, and this coupled with being really shy around women who I’m interested in, isn’t making my life easy. I’ve only been on about four dates since high school, and none of them worked out. I feel all I need is practice, but I get so nervous on a date, that rather than confronting my fears, I’ve been avoiding them. Even something as simple as kissing is foreign and scary for me, as I’ve never kissed a girl. The guy is supposed to take the lead, but this guy hasn’t got a clue!
I was a big teenager, so I never had great self-image and lack confidence. I lost a fair bit of weight, but being big has left it marks both on my skin and on my confidence. My family also moved often so I never had any lasting friendships and the lack of friends has followed me into my adult life. I’ve always felt like the odd one out, and as each year passes it seems to further diminish any romantic confidence. I know I’ve got love in me and much to share, but I don’t know how to find someone to share it with. — 32 Year-Old Virgin
First of all, you need to know that you are not alone in feeling the way you do. I get countless letters from people of all ages — yes, even older than you — who have never dated, don’t know how to date, and feel insecure about their lack of relationship experience. What you need to keep in mind is that there are women out there who are just as anxious about finding you as you are about finding them. So, how do you find each other? Well, casting a wide net is a helpful start. In your search for love, don’t rule out women who are older or younger than you, or don’t look like a movie star. Look for someone you can connect with on an emotional and intellectual level first before exploring how well you connect on a physical level. And treat women the way you’d like to be treated — with respect, sensitivity, kindness, and understanding.
As for where to look for these ladies, online dating was made for someone like you. You get to make your first move from the comfort and security of your own home! You can take your time forming thoughtful questions and responses in your emails, and you’ve got a wide array of women to choose from. Since you were once heavy and say the weight left it marks both physically and emotionally, I’d suggest you check out some dating sites specifically for heavy-set people (BBWCupid.com and OverweightDate.com are good ones). Even if you aren’t overweight anymore, you may find comfort in meeting people who appreciate the struggle you’ve experienced with your weight and the effects it’s had on your self-esteem. You might even be able to inspire others with your story of weight loss, which could serve as a real confidence booster for you.
Once you’ve had enough email — and perhaps phone — interaction with a woman (about three emails each should suffice), ask her out for coffee or a bite to eat. Don’t get so comfortable in your online exchanges that you avoid meeting up in person. From there, you’ll be able to tell whether you have enough chemistry to give a second date a shot — and even if you don’t, perhaps you like each other enough to be friends, which is something you could use more of, right? When it comes time to make a move, don’t over-think it. Be confident! You didn’t know how to walk the first time you took a step, right? You didn’t know how to drive the first time you sat behind the wheel of a car. You didn’t know how to ride a bike the first time you pedaled down the sidewalk. But, sure as shit, you probably do all those things with aplomb now. Kissing — and everything else — is the same way. You’ll figure it out. And if you’ve got a good and caring teacher to show you the ropes, you’ll have fun learning.
*If you have a relationship/dating question I can help answer, send me your letters at firstname.lastname@example.org.