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Ask Sassy: Dating advice for a guy who asks “How can I get some?”

In Living, Style by Guest Writer2 Comments

Sassy dishes out dating advice for a guy who needs to know what it’s like from a lady’s point of view.

holding hands

Dear Sassy:

I am getting divorced after 13 years. Besides my wife, I’ve only ever dated one other time. Since she left, I’ve been on over 30 first dates, and gotten pretty good at them. I’ve even had some nice second dates, too. The problem is that when I am attracted to a woman, I’m unsure of how to get physically intimate. When it seems time to kiss her, I worry that my breath is bad, or that she’ll think I’m too forward, or that I’ll do something wrong. How do I know when it’s time to make a move?

Dear Gunshy:

First off all, +1000 to you for not being a douchebag. The fact that you are asking this question at all makes me want to introduce you to all of my single female friends and say “Go at it, ladies, may the best woman win.” I’m sure I’m not alone in saying THANK YOU for caring about the right thing to do.

Also, sidebar about your breath. You are so super right on about worrying about your breath that it isn’t even funny. I was once attracted to a very handsome fellow who was smart, kind, polite, and sexy, but his breath was tragically horrible. So bad that every time I forgot about it and was attracted to him again, I’d catch a whiff and it would turn me right back off. I suppose I could have offered him a mint or something, but the lethal scent was enough to make me not care anymore. A woman’s sense of smell is a formidable opponent…or something you can use to your advantage. So mouthwash up, sweetheart, and use a light touch on the cologne.

Short of putting up a blinking neon sign that says “TAKE ME NOW,” what are some ways that you signal to a date that you’d like to get busy with him?

The trouble is, there isn’t one magic formula that you can use to figure out how to properly cozy up to the right lady. Sure, there are signs that she’s into you — when she twirls her hair or looks at your mouth more than 3 times per minute or when she pushes you up against a wall while you’re walking and covers your lips with hers — but I get that a man who has been in a relationship for 13 years comes with a lot of baggage and confusion. Reentry into the dating world after such a long time can be scary and loaded with mines. Without those clear signals that it’s go-time, it can be hard to judge.

Okay, I lied. There is a magic formula, but it’s not an easy one to use. You’re going to have to wing it. Use a combination of your own feelings of attraction, physical cues the ladies are throwing up, and your moral code. Getting this right is going to take some practice. You’ve already geared up for this during your mind boggling number of first dates. Now it’s time to relax and not be so anxious around women.

Don’t try to make a move just to make a move. Take time to pay attention to the chemistry between you. First be sure that you want to — that you’re into her, as the kids say. Otherwise you’ll be veering off your chivalrous path and going after some nooky just for the sake of physical pleasure, not necessarily in service of building a loving relationship. And you don’t want to lead the ladies on. That would be unfair and in this crazy world it could also blow up in your face later.

If you spend enough time with a woman you like and you pay attention, you will start to sense what she wants, and you’ll understand better what you like, too. Does she like to hold hands, is she a hugger, does she snuggle up to you at movies, kiss you hello when you pick her up? Is that even something you want to do with her?

I’d like to open this one up to my lady friends now. I know a lot of you are single again after being married, so tell this great guy what you think. Short of putting up a blinking neon sign that says “TAKE ME NOW,” what are some ways that you signal to a date that you’d like to get busy with him?

Send in your problem for Sassy to solve, whether it’s a parenting question, relationship dilemma or a snafu with social etiquette and it may get answered in a future column. Sassy is here to help! Submit your question for Ask Sassy here! (Or just email me, darling. We can keep it between us.

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  1. I make it clear if I’m into a guy which is to say, rarely. BUT, if I am, I am much more touchy feely, I will lean in when talking to him at dinner and then if that doesn’t do it, I just jump the guy … in my mind.

  2. I’d say I’d be leaning in more (not Sheryl Sandburg style), making eye contact and smelling good (perfume & mint). He should be doing similar motions, making eye contact and showing genuine interest. I’d say better slower than faster though. You don’t need a kiss on the first date but by the fifth it’s time to get a move on.

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