Dating coach Connell Barrett answers your questions on what to do on a second date, the right way to approach, and 7 secrets to asking a girl out 

WHAT TO DO ON A SECOND DATE

I want a girlfriend, and I’m looking for tips on what to do on a second date. My first dates are good, but on the second date or the third things seem to stall out. I feel like I want things to go well a bit too much. Any tips?

—Sonny, 27, Los Angeles 

The stakes are higher on the second date because it’s the gateway to a potential relationship. Date 1 is about seeing if there’s chemistry and mutual attraction. On the second date (and beyond), you’re deciding if you’re a good fit for the long-term. 

As for what to do on a second date, the stakes are higher, but don’t try too hard. I tell my clients: To impress, do less. 

I don’t mean not to try. Just don’t try too hard. Many guys feel the need to “up their game” on big dates. They plan elaborate activities or spend a bundle at a white-tablecloth restaurant. This can backfire because trying too hard can convey neediness, which kills attraction. 

Don’t try harder. Rather, go deeper. On second dates, try to connect over Big Life Stuff: careers, religion, wanting kids, politics, your core values. When you and a woman find that your Big Life Stuff aligns, it’s easier to move toward being a couple. 

Another tip for second dates: Make sure you’re circling the bases. If there’s no physical connection by the end of Date No. 2 (a kiss, at least), something is off. Either it’s a lack of chemistry, or someone is not making moves—likely, you. 

Women want to feel like things are progressing, or else she can lose interest. In terms of physical connection, try to keep moving forward. The pace around the bases doesn’t matter. You can be Rickey Henderson or Big Papi. It’s all good, as long as you’re not stalled on first. 

HOW TO APPROACH WITH CHARM

Connell, I love your philosophy about being “radically authentic.” I like to approach in a direct, honest way, but I think I’m too direct. I say things like, “You’re sexy” or “You’re gorgeous.” It can freak women out. Am I coming on too strong?

—Dan, 34, Pittsburgh 

Dan, with approaching there’s nothing wrong with being direct. The thing is, a beautiful woman is used to men commenting on her looks. She may be complimented, but if your reason for talking to her is looks-based, you may seem like all the other guys who hit on her. And she may feel objectified as well. 

Here’s a new way to approach—it’s direct and elevates your status. Simply say, “Hi, I just saw you, and I had to share my awesomeness with you.”

Rather than wanting to “take” something, you’ve changed the frame. You’re offering something—namely, your awesomeness. This sends the right messages and vaults you to the top 1% of men. You’re sharing something, which is elegant and classy. 

It also shows massive confidence, and beautiful women love confident men. 

ASK AND YOU SHALL RECEIVE

I always get stuck in my head when asking a girl out. I’m not sure what to say or how to ask. Got a tip?

—Dominic, 39, New Orleans

A tip? No… I have seven tips! Here are the essentials to asking a woman out for a date. 

1: Never say, “So, what do you want to do?”

Women love a man with a plan. Lead! 

2: Suggest your idea with confidence

(“I know a place you’re gonna love . . .”), but make sure to listen to any objections she might raise and adjust accordingly.

3: Harness the power of the word “let’s”

This allows you to lead in a non-bossy way (“Hey, let’s grab a smoothie . . .”). 

4: No wishy-washy nonsense like, “If you want to” or “If you have the time.”

Assume she’s into you! 

5: Choose a location that’s convenient for her to get to. 

6: Don’t start tossing out possible days for the date.

If her schedule is busy, she’ll have to keep turning you down (“How about Monday? . . . Okay, Wednesday? . . . Maybe Thursday?”), which makes you look too available and too eager. Instead, give her a window of time, and use this magical phrase: “What day(s) works for you?” This way, she’ll tell you when she’s free. 

7: Add a sweet, sincere comment such as, “It would be cool to finally meet you.”

Remember: It’s not about the wine or the karaoke. It’s about the two of you getting closer. 

When you put it all together, asking her out will sound something like this: “Hey, Rebecca. You like red wine, so . . . Let’s grab a couple glasses this week. I know an awesome spot not far from you. It would be cool to see you. What night works for you?”

Now you have second date advice and tips on asking a woman out. Here are 5 questions to ask on a second date to help get things moving. Ready for date number three? Try this advice on what to do after a second date. If you still need first date advice, check that out here. Have another question? Ask it below.

Connell Barrett is a NYC dating coach for men. He's helped men all over the world find the women of their dreams with dating advice such as how to get out of the friend zone. He's been featured on The Today Show and Access Hollywood and in publications like Maxim, Cosmopolitan and O Magazine. Follow Connell's column and ask the dating coach a question below.