Pinings — Advice by Sherry Hughes

Falling Short

Dear Pinings,

I always feel as if I fall short when it comes to having sex with a woman. I’ve been with many women but never more than a date here or there. I’m a good-looking guy with a good job. I go to the gym every day and even though I still live with my folks, I’m plenty independent. For some reason, I never manage to get the second date. If the first date ends up in bed, I never see the woman again.

I don’t want to talk to my friends (male friends) about it because they’d just laugh it off (I’m getting laid, why complain?). But I want more than a lay here or there. I don’t want to get married or anything, but I’d like to hang out with someone, maybe travel together.

If anyone knew I was writing to you, I’d be humiliated.

- Ian

Dear Ian,

I won’t tell anyone you wrote to me.

It’s hard for me to figure out what you may be doing wrong or right based on what you tell me in your letter. And even if I got a complete history of your dealings with women, I still might not know. I’m going to give you some advice that will be challenging, but will probably give you some of the answers you seek. Find out where the women you’ve dated live or work. See if you still have numbers or e-mail addresses and contact them. If you invite them to have a drink or coffee, be sure to explain to that this isn’t about a date, just a talk about something important to you. If they feel better e-mailing, fine.

Ask these women what they thought of you and encourage them to be honest. If  you can, ask them about the sex—was it fun, was it terrible, was it boring? Ask them how you were as a date. Were you caring and kind? Fun to be with? Self-centered? Cheap?

You might struggle to do this. That’s OK. You just have to decide whether this is something you want to really learn about yourself or you’d rather stay on the path you are on — never getting a second date.

Let’s face it, our friends say nice things to us. Our family says nice things too. If we want the truth about how we are as lovers, friends or as romantic partners, we need to ask people who have shared that experience with us. As I said, this will be tough. But it will also be a learning experience for you. And it will allow you to move on.

Sherry Hughes welcomes letters from readers. Contact her via e-mail at sah103@hotmail.com