You know when it’s coming. It’s the man who lingered by your side all night at the bar. The coworker who finds any excuse to email you. The classmate who just won’t leave you alone. It’s never the men you want; often the mommas boys, the gangly awkward ones, or worse the you’re-lucky-I’m-asking-you-out type.

Mr. I’d Rather Be Single can be persistent can’t he?

My friend Ashley gave me permission to share her story & actually prompted this blog post.

A few weeks ago, Ashley ventures downtown in Nashville with a group of girlfriends.

Two things you should know about Ashley to understand the scenario:

#1: She’s gorgeous {tall, blonde. . .you get the picture}.

#2: She’s really nice & cares about people.

Enter Mr. I Like to Talk About How Much Money I Make. We’ll call him Sam.

Sam and Ashley’s friends start mingling and within minutes Sam has his heart set on getting Ashley’s number. He walks over and makes awkward conversation about money, popularity, and potential places he wants to take her. She immediately knows he’s interested and tries to engage in the conversation happening across the table from her. But to no avail. Sam is persistent.

Ashley goes to the restroom and tells a friend to get Sam away from her. He is coming on strong and Ashley doesn’t know how to get out of the situation without hurting his feelings. They return from the bathroom and Sam is standing there. . .waiting.

“Hey, give me your number so we can go have drinks sometime,” he says holding out his phone.

“Uh. . .well. . .” Ashley stumbles over her words.

“Thank you, but I’m really busy. . .and. . .” she mutters finally. But he persists.

Sam proceeds to ask Ashley a series of “why not? You don’t even know me!” questions and Ashley is incredibly uncomfortable. Finally, she agrees and gives him her number because she doesn’t know what else to do. The man would not leave a sister alone!

The next two days, Sam called & texted Ashley in a rather frenzied manner attempting to set up a date. She {a little freaked out} responded and firmly told him ‘no’.

These situations can be incredibly difficult to navigate, especially when the man on the other end happens to be a really nice guy. How can you say ‘no’ to a man without taking a blow to his ego? Is it better to go on one date and give Mr. I’d Rather Be Single a chance?

Let’s flip the scenario around. How would you like it if a man took you on a date because he didn’t want to hurt your feelings. What if the next date you went on, the man told his buddies:  ”She’s really not attractive  and I couldn’t possibly imagine a future with her-but I took her out so she’d feel good about herself.” It’s dishonest and inconsiderate, isn’t it?

I’m a people pleaser, so I’ve said ‘yes’ to my share of dates that I had ZERO interest going on. In the flurry of people-pleasing, it’s often hard to be authentic. But authenticity always shows strong character.

So how do you say ‘no’ to a man?

1.) Be kind. It probably took him a lot of courage to ask you out.

2.) Don’t make a big deal out of saying ‘no’. Say it nicely and transition smoothly to another topic.

3.) If he presses you for a reason (this is always awkward), tell him the truth. The REAL truth. “You’re a great guy, but I don’t see you in a romantic way,” is a great line.

A sympathy date really doesn’t do anyone any favors. If you’re breathing and female, you’ve overanalyzed why a relationship didn’t work out when everything seemed “perfect”. Am I right? Wouldn’t it just be easier if he was direct and told you why he stopped calling, never called, or broke it off with you? In the fashion of the Golden Rule, apply the same kindness you want to see from the men in your life.

Do you have a hard time saying ‘no’? Have you found other helpful ways to say ‘no’? What dates have you been on just because you didn’t want to hurt feelings? 

If you liked this post, you may also like:

• Mr. Promised He Would Call & Mr. Inconsistent
• Why Women Text Back
• Mo’ Money Mo’ Problems | On Learning Generosity
• “What Most Surprised You About Marriage?”