My husband is 59-years old. He has the rare distinction of never being turned down when he asked someone out. Never. Not even by me. I had a rule that if a guy had the guts to ask me out I would say yes because he already knew I was a pastor. Who wants to date a pastor? Apparently John did.

We’ve been married over 20 years now and he is 59. That is a lot of years he did the asking and never got turned down.

When I am talking to the many young adults I talk to, he voices his frustration at the excuses he overhears about why they aren’t asking people out. Or he will burst into our conversation when he is present with the bold encouragement to simply ask. It should be noted here that he did not grow up Christian so he doesn’t have any of that weird Christian messaging about dating in his head.

The following is my interview with this rare man who has never been turned down who is full of opinion about this topic. His prevalent attitude about this definitely affects my advice to those who ask me. He is that vocal about it.

Q:  Why should someone ask someone else out?

John:  Why wouldn’t someone ask someone out? I can’t think of a single reason why not asking might be better than asking. If you don’t ask, the answer is “no.” If you ask you have a chance.  If you connect with someone the only way to get to know them better, to see if a relationship can develop, is to take the risk.  Someone recently said to me, “If I don’t ask then in my mind I could convince myself the answer may have been a ‘yes.’ But if I ask and get turned down then I know I wasn’t good enough.”  You’ll try out for the band or the football team and you’ll interview for a job but you won’t ask someone out because you’re afraid of being deemed not good enough? Who made the cute girl more important than the football coach, the potential boss or the band leader? I don’t understand this logic.

Follow up comment:  Sounds like you have read my articles where I have repeated often, “A failed date does not define you.”

Q:  Were you ever nervous when you asked someone out?

John: Of course. Anytime you take a risk there’s a chance you can be hurt or embarrassed. I’ve done many things in my lifetime that I was nervous about doing.  But not doing those things is way worse than trying and failing for me. The “not knowing” is impossible for me to live with. I’ve been nervous starting a business, trying out for a sports team, in job interviews and playing music–so asking someone out is no different. It’s a risk.

Q:  Were you ever afraid of being turned down?

John: I wouldn’t say I was ever afraid. The “what could have been” if I didn’t ask was much more frightening. What if that was “the one” and I let my fear get in the way of that? What if that absolutely “was not the one” and I never knew? I don’t like to leave potentially good things unanswered. And if I’m being completely honest I have just always believed I was good enough for anyone. I know I have flaws and I also know anyone that I would ask out has flaws as well, even if they hide them better than I do.

Q:  How do you think you would have handled being turned down?

John:  I have enough self-esteem (ego) to handle being turned down. I fail at a lot of things and it doesn’t prevent me from trying more. But I’m sure I would feel embarrassed for a few minutes. No one likes to be turned down for anything.

Q:  Did you ever ask someone out who you thought was “out of your league”?

John:  Always. I learned a long time ago that if you expect small things in life you’ll get them. I’m not a fan of settling. I’ve always wanted to squeeze every last drop of life out of life. But the real answer to this question is why would I think I’m not in someone’s league? I feel like there’s no league I don’t belong in, and that’s how everyone should feel. I think in a lot of ways we become what we believe we are. If you think you’re not worthy of something you’ll speak that into reality and you really won’t be worthy. This “never being turned down thing” isn’t about anything other than being bold and taking a risk. You’d be surprised at how easy you make it for someone to say “yes” when you just ask.

Q:  Why did you ask me out?

John:  Because you were intriguing to me. We had a lot of very deep conversations before we ever dated and it’s important for me to be with someone that isn’t shallow. You’re the opposite of shallow and I knew that right away. It didn’t hurt that you were (and are) a beautiful blonde either (smile).  And what would the last 21 years of my life look like if I didn’t ask? I could have found a dozen reasons not to ask but I chose to ignore those. To be clear, asking someone out is just a decision. It isn’t rocket science or brain surgery and you don’t need to ponder for months. When I was a teenager I just decided if I liked someone I would ask them out. I made the decision to do it before I even had anyone in mind to ask out.

Q:  What frustrates you when you hear the trepidations of others who are afraid to make the move?

John:  All of it frustrates me. I don’t understand why people (men) put so much value in someone’s opinion that doesn’t even know them. If you ask someone out and they say “no” it is literally no reflection on you. If you think you’re not good enough, smart enough, handsome enough or anything else enough you’re already handicapped. People can sense your confidence and self-esteem or lack thereof. So why do you have no confidence? Fix this issue and you’re on your way to a different and better life. Stop treating yourself like a second class, unworthy citizen.

Q:  What lasting advice do you have to give?

John:  Have you ever seen what looked like a mismatched couple and thought, how did she say yes to him? He asked and you didn’t. It’s that simple. If I could bottle and give away one thing I do well it’s this: I know God made me in His image and I’m not about to concede anything to anybody. You’re better looking, I’m smarter. You’re smarter, I’m a better listener. You’re a better listener, I’m a better server. You’re a better server, I’m kinder. We can play this game all day and night and you won’t win. And this should be your attitude as well. Forget the nerves, the possible rejection or the embarrassment. Be the one that makes people say, how did he get her?

One last thought/story: I once asked someone out that I thought was way out of my league in many ways, because even I have moments of doubt. (Smile)  She worked in a job where she had contact with people every day, all day long. When I asked her she said, “Wow, yes! I’ve been working here for five years and you’re the first person to ask me out.”

Get out of your own way and take a risk.