Advice Goddess

Q: I've been on three dates with a gorgeous, funny, kind, and successful woman. Two weeks ago, we met for drinks with a group of my friends, and a guy in our crowd who’s in the habit of saying crass things showed up. He ended up insulting her by making a rude, totally vulgar sexual remark about her. He was trying to be funny, but I could see she was offended. I was so taken aback that I didn’t say anything. Shortly afterward, she said that she had to leave. I walked her out and apologized for him, and I have since apologized by email and in three voicemails. I’ve tried to set up another date so I can apologize in person, but she keeps getting off the phone really quickly. Would sending flowers to her work be appreciated or seem creepy?

—Friend’s Foot In My Mouth

A: Life sometimes presents you with a chance to show a woman what you’re made of, like when some creep aggressively disrespects her in your presence. Your response — staring into your beer — told this woman a lot about you, like that you’re the sort of boyfriend who would take her camping and, upon hearing a bear crashing through the woods, tuck a hot dog in her pocket and shove her out of the tent. 

If your initial response wasn’t enough to make her never want to see you again, you probably sealed your romantic doom by taking immediate inaction in the wake of your inaction. Sure, you did say you were sorry…and email her that you were sorry and leave her multiple voicemails saying that you were sorry and then flap your lips some more and try to ask her out to say you’re sorry in person. Unfortunately, there’s a difference between a meaningful apology and regret-flavored borderline stalking. 

Sending flowers — immediately — might have been wise, as a number of studies find that people are more likely to be forgiven, even for serious transgressions, if their apology is accompanied by a gift, which says that they value the person they hurt enough to invest in repairing the relationship. But no amount of flora will solve what I suspect is the real problem here: She probably now sees you as a passive wimp who responds to even a minor challenge by folding like a sheet of typing paper. (If you have a favorite blood sport, it’s probably crocheting.) 

You didn’t have to challenge the guy to a parking lot duel. You just needed to say something — perhaps just a stern, “Dude, you’re really out of line.” Even women who can defend themselves just fine want a man who’ll stand up for them. Being a stand-up guy comes not out of memorizing a list of the right things to do but from becoming a person who can’t help but do them. This, in turn, comes out of personal standards for courage, generosity, fairness, and integrity. Of course, in order to assert these standards, you’ll need self-respect. If that’s a problem area for you, pick up “The Assertiveness Workbook,” by Dr. Randy J. Paterson, and “No More Mr. Nice Guy,” by Dr. Robert Glover. Put in a year manning up, and if happy hour again becomes insulting hour, you’ll take action — and it won’t be scurrying to the nearest florist to ask, “Excuse me, but which color roses say ‘I’m a man who will rise to the occasion instead of hiding under the table’?”

Q: I’m an accomplished, caring, sensitive, and funny guy. I do well talking to women in social situations where I’ve had time to warm up. I’m not great at approaching women on the street. How can I increase my street-side “swagger”?  

—Need Game

A: The stride itself — that wide-legged rolling gait — isn’t hard to adopt. Just pop a sleeping gerbil in your underwear. But you’re probably talking about the street meaning of swagger: self-assured cool. That’s a way of being that you can’t just throw on like a sweatshirt. Guys who try to put it on usually end up coming off cartoonishly cocky. Sometimes what’s most endearing about people are the small ways they aren’t totally put together, especially if they’re gutsy enough to put themselves out there, flaws and all. So maybe talk to compelling women you see on the street — a tough audience for any guy — but do it as you, not with your best imitation of Jay-Z. And accept that your natural hunting ground is probably your local coffeehouse, where you won’t have to charm a woman before the light changes and she won’t immediately suspect that what you’re really saying is, “Hi, I’m a purse snatcher, and I was wondering if I could distract you with some small talk while I root around for your wallet.”

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