We hate spam as much as you do!

Are You Smart, Successful, But Still Single?!

Find Out The Top 3 Mistakes You're Making That Ruin Any Chance At Love
And Take Control Of Your Love Life. Download your FREE eBook NOW!


We hate spam as much as you do!

Dr. Aesha,

I met this guy. He’s nice, but during our dates he keeps talking about work and sometimes I get bored. I feel he is nice but just doesn’t know how to date. In fact, on our second date, he told me he wasn’t comfortable with dating. Do you have tips to help? Should I just move on?



Let me help you distinguish between a bad date and an awkward date, so you can decide if you want to give him another chance.

True story. A sister went on a first date with a guy she met online at a coffee shop. He greeted her by saying “hey,” barely looked up from his laptop, and spent the entire date showing her pictures of his house!  He never even offered to buy her coffee.  

This is a textbook “bad date”  and if this sister is smart, she won’t give this guy the time of day!

But what about an awkward first date?  You know, when there are long, awkward silences in a conversation, or the conversation is boring because he keeps talking about work ? Or what about the nervous tension you feel when he gushes over how amazing you are, and he can’t believe you actually said YES to a date with him? Should you give him another chance or do you just bounce to the next guy?

If you’re anything like my clients, you might be quick to say NEXT and go back to swiping on SoulSwipe.

But what if I told you that some folks stay in relationships past the expiration date, but too many sistas move on TOO FAST!

Let me help with that: dislikes are not dealbreakers. If it’s something that can be changed (& he’s willing to step up), then it’s worth a second change.

Tip #1: Bring Your Own Chicken Wings To The Date

 (Wait, huh?)

No, sis, I’m not telling you to bring food to a date. I’m using this as analogy.

Imagine there was a potluck at your office and you realllllly want some lemon pepper chicken wings. You spend 7 days hoping and wishing and expecting there to be lemon pepper chicken wings there. You arrive, look at the table, and DARN! There’s some hummus, a veggie platter, and potato salad with raisins in it. (Yup, Becky with the good hair made it).

So you spend the whole time being resentful and not enjoying yourself, when the solution was simple. Bring your own chicken wings and you guarantee the you have at least one thing you like.

In dating, you can have an unfair expectation that the man shows up to entertain you. You want him to “make you laugh” and to help you escape the stress of the day. But how can he tell what will impress you on the first date?

You are responsible for the energy you bring. If you want an enjoyable experience, make it one. Suggest a restaurant you love. Give him ideas of the activities you’d like to try. Do everything within your power to ensure YOU will have a good time. That way you’ll never waste your time and you won’t put so much pressure on the other person to blow you away on the first meeting.

Tip #2: Break The Ice With A Warm Greeting

Use your feminine allure to warm up the date before it gets started. Don’t just shake his hand or give a professional “hello.” It’s a date, so it’s ok to give a friendly hug. (If you’re worried about sending the wrong message that you’re looking for a hookup, then you need to read this post and this one).

If you notice he looks nervous, just acknowledge it! Say something like: “Man, your photos don’t do you justice. You look great. And you smell good too!” OR, “First dates are so nerve-wrecking, don’t you agree? I’m glad we’ve finally met in person, though. You make me feel comfortable.”

The point is to take the expectation off of him and to use your feminine leadership skills to nurture and connect so that he feels good. You’ll get him to open up faster and that means one of two things:

  1. He’ll be transparent and you’ll see he’s not the right one for you.
  2. He’ll be grateful and make a connection with you (and want to see you again!)

Tip #3:  Play Curious Vs Acting Like An Investigator 

You mentioned your date keeps talking about work and it’s boring to you. Well most people don’t know what to talk about on a date, especially if he’s trying to impress you. He’s defaulting to what he knows.

You can create a fun conversation by asking great questions.

Try This: The solution to this common dating problem is to be genuinely interested in your date. The person you’re having coffee with has a lifetime of experiences you haven’t discovered yet. Be curious, ask him to share stories with you, and find 2-3 things you really appreciate about him. You’ll find that the conversation will flow more easily and you’ll actually have a good time together.

For example, ask him what he likes and dislikes about what he does for a living; ask him to tell you stories of the funniest thing or most embarrassing that’s happened to him. Ask him to tell you about his most memorable childhood experience.

And if you get stuck, here’s your go-to phrase: “tell me more about that!”

Be open to the answers. Don’t judge. You may not ever see him again, but you’re having a meaningful experience right now that is leading you to the love you want.


Awkwardness isn’t always a sign that the guy you’re dating isn’t into you.

He may just be nervous or have a shy personality.  In fact, he might like you a lot!   I remember the first official date my husband and I went on was at a movie theater after Thanksgiving dinner. Even though we’d gone to coffee several times and had spent quite a bit of time talking on the phone, something about this date made us both nervous. Maybe it was the nervous way he blurted out “do you wanna go out?” Or the silly way I said “sure!”  We decided to go to a movie and of course all I could focus on was not passing gas!  At the end of the date, he dropped me back off at my parents’ house and we stood there for a few minutes before hugging each other good night.  Can anyone say, aaaaawkward?!

But, a few minutes later, I called him to tell him I had a good time and told him he could call me anytime.  The rest, they say, is history and we were married 11 months later!

An awkward first date can surpisingly lead to an amazing relationship. 

Have you ever had a less-than-stellar date that turned into a great relationship? How did you decide to give him another chance? Please share in a comment below