Dating coach Connell Barrett answers your questions on spicing up first dates, the secret to quality matches on Tinder, and how “ugly” guys can attract beautiful women. We'll start with 5 flirty first-date questions that'll take you from connecting to romancing.

Flirty First Date Questions

I have a lot of nerves and anxiety before a date because I’m not sure what to talk about. I worry that I’ll run out of things to say and the girl will get bored. What do you suggest?

—Chuck, 47, Seattle

Chuck, I kid you not: I used to be so nervous before dates about what to talk about that I brought notecards, and I’d peek at them while I was in the bathroom. 

Now, I’m NOT suggesting you prepare topics to talk about (it’s a date, not a Power-Point presentation). But it can help to have a few flirty first-date questions in your proverbial back pocket. 

Here are five flirty questions to ask a girl that will help you have great conversations on dates. If you ask them (more or less) in this order, you’ll take the conversation from light and friendly (early on) to fun and flirty (later in the date). 

“What’s your dream travel destination?” 

Talking travel works! In one study, 18 percent of couples on first dates who discussed travel wanted to go a second date. In contrast, less than 9 percent of couples who talked about movies were interested in going out again. 

“Who should play you in the movie of your life?” 

This playful question caters to her ego—and the actress she chooses will clue you in on how she sees herself.

“Who’s your celebrity crush?” 

Now you’re discussing romance, which is way better than talking about weather or politics. 

"Would you rather make out on a couch or against a wall?"

Now you’re putting hot-and-heavy images in her mind, dialing up the sexual tension. 

"Where’s the one place you’ve always wanted to hook up?"

Again, don’t START with this question, but if you lead up to it, you might find out that you both want to, say, go to the beach at night and get sand in naughty places.

Asking the right flirty first date questions can help create a vibe that leads to amazing dates. My client Patrick had been struggling with first-date connection, but he used these questions to dial up the romantic tension with a woman he met on Hinge, and she asked him, “How about we go back to your place?” 

Now THAT’S what I call a flirty first-date question. 

WINNING THE MATCH GAME

Help! I’m not getting any matches on Tinder and Bumble. It’s frustrating! What’s the likely cause? 

—Christopher, 45, Cincinnati

The probable culprit? Mediocre photos, starting with your featured shot. 

If your first photo doesn’t instantly hook a woman’s interest, she likely won’t look at the rest of your profile. Rather, she’ll keep swiping. A lead photo that doesn’t resonate with women—say, an unflattering selfie or a poorly-lit shot—can crush your results. 

The solution is to have a vivid, magnetic portrait as your featured photo. A quality portrait can be a game-changer and has the following key elements. 

• The image should be crisp, clear, and bright, ideally shot in natural light.
• Zoom in close and shoot from the waist or chest up. 
• Look at the lens; eye contact will increase the sense of connection with your audience.
• Dress AMAZINGLY well. Wear what you would for a first date. No sweats, no caps, no cargo shorts—no exceptions. 
• Smile an authentic smile. (Leave the smoldering glares to Zoolander.) 
• No shots of you holding a fish, fellas. Women don’t want to date Quint from “Jaws.”  

Upgrading your featured photo can have dramatic results even without any other profile tweaks. My client Kevin—an attractive, eligible, divorced healthcare worker in his forties—was struggling to get matches. The problem? His first photo was a shadowy, grim-faced selfie that he’d snapped in his garage. (He looked like Dexter in his kill room.) 

Kevin upgraded to a handsome, sunny outdoor shot, showcasing a big smile and a pressed, powder-blue button-down. Within a day, he had fourteen matches that he was psyched about.

THE UGLY TRUTH

I’m desperate, and I need help. I’m ugly, bald, and I’ve never had a girlfriend. I’ve only ever had a few dates. I just feel like I have no options, and it makes me feel lonely and hopeless. And when I compare myself to all the guys I see with girlfriends, it makes me feel even worse. I’ve been putting off the whole “dating thing” because I’m not sure where to start. Help! 

—John, 36, Austin

John, thank you for being so honest. I honor that. What you wrote was brave as fuck. It’s not easy to admit that you struggle with women and that you’re lonely.

I know how you feel. I’m no pretty boy, either. (I look like a cross between Willem Dafoe and a Ron Weasley.) Like you, I was in my 30s when I realized I had no dating prospects, and ZERO confidence in myself. 

For me, my low point was when my wife—the one woman who wanted to be with me—dumped me after just nine weeks of “marriage.” I felt rejected by ALL women. I assumed I would always be alone, or have to settle for a loveless marriage. 

I was wrong, of course. I totally transformed my love life, and you can, too. 

Some great news: You don’t need to be good-looking to get dates and find a great girlfriend. 

You see, women are attracted to authenticity MUCH more than they’re attracted to looks. They want a genuine man who knows who he is. Sure, looks are a nice bonus, but it’s just not essential. 

Feeling that you’re ugly is one of the biggest confidence crushers for a guy. Men put way too much importance on looks. We project our looks obsession onto women. Men prioritize visual beauty, so we assume women do the same. But women are more attracted to behavior, confidence and intelligence—and the magical X-factor of authenticity. 

A guy can look like either Brad Pitt or Brad Garrett, as long as he's an authentic man who has something to offer. 

So, John, first things first: You need to stop comparing yourself to other guys. Instead, compare yourself to the guy you were yesterday, and be 1% better than him… every single day. Keep growing. An evolving man is an attractive man. 

Also, you need to begin taking action to boost your confidence, and become more attractive in ways that you can control. 

Develop your sense of humor because women love to laugh. (Take an improv class.) 

Become a better, more present listener because women love to be heard. 

Communicate in a more expressive, less filtered way because a man who “tells it like it is” is magnetic. 

Take up an awesome, cool hobby you have passion for because women love a guy who follows his passions. 

Make sure you have great style, because your looks don’t matter, but your LOOK matters… a lot. 

Shift your focus from what you think you lack to what you offer. This will transform your confidence. 

If you lack great looks and a 6-pack, don’t worry. Sculpt a 6-pack personality. 

Final thought: Don’t put this off anymore. These problems don’t fix themselves. Procrastination is a creditor who charges interest in the form of loneliness and low confidence. 

Do something. Take action. In the words of the Bard: “Action is eloquence.”

Want more first-date advice or tips on how to text a girl the right way? Read more of Connell's Ask The Dating Coach column and subscribe. Need to know questions to ask on a second date? Click here.

Connell Barrett is a NYC dating coach for men, helping men all over the world discover how to get a girl in an authentic way. He's assisted thousands of men in connecting with the women of their dreams. Connell has appeared on talk shows such as Access Hollywood and The Today Show and in publications such as Maxim, Cosmopolitan, O Magazine and more. Ask Connell a dating question below.

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