Navigating Difficult Conversations

We live in a time where our digital connection is 24/7, yet feelings of aloneness run rampant. The curious thing about aloneness is that we all simultaneously feel it and contribute to it. Standing someone up, ghosting, and icing perpetuate a dismissive dating and social culture where it’s the norm to bail before the big talk.

Our Kelleher Matchmaking clients are fortunate to have a personal matchmaker to mediate a delicate conversation for them after a first or second date. However, once a real connection is established, we do encourage clients to manage the difficult discussions on their own. Here are a few insights to set you up for success.

“When a person doesn’t want to continue seeing someone after a few dates, it is always difficult for that person to communicate the message. Most often the attraction isn’t mutual, or things just aren’t clicking smoothly and naturally. Regardless, it’s human nature to take the rejection personally which makes uttering the words feel terrible. As matchmakers, we take great care in making sure the dismissed person knows there’s nothing wrong with them, they simply didn’t fit someone else’s criteria. Most times it truly is nothing personal,” explains Patty Russell, Kelleher matchmaker.

An important thing to keep in mind is that in the dating world rejection is an even playing field. Kelleher Chairman’s Group matchmaker Molly Davis explains, “Everyone you meet through a firm like ours or an app is actively dating and will at one point or another be on the receiving end of the “You’re not my person” news. I think it’s best to offer honest, thoughtful, gracious feedback. Draw from your own experiences of being on the receiving end of uncomfortable feedback. Use whatever tactics feel best to you and offer others that same courtesy. If you’re not sure how to start the dialogue, I suggest something like, “I respect you and want to be as candid as possible…”

Kelleher matchmaker Pam Nolen reminds us that timing and delivery are critical. “Wait for a time that’s right for both of you – when you both can focus and be present. Be sure to choose a location where you can comfortably speak. Be honest, direct, and use simple statements. Telling the truth will feel bittersweet and even though it may hurt the other person to hear the difficult news initially, time will take care of healing their heart.”

It’s not easy to give or receive unfavorable information. Dig deep to accept the difficult news with grace and find the lessons buried in the experience. Matchmaker Patty says, “I work with a client who recently had a tough time knowing the person he just met didn’t feel a romantic spark for him.  He’d put time and energy into creating a special date and ended up spending a few days with the woman. It simply wasn’t a connection for her and she shared her experience in our post-date follow-up. As matchmakers, we’re able to learn more about the “why” that people are often afraid to share with the other person. In turn, we share important tidbits that can be extremely helpful for both parties moving forward. There is always something positive to take away from any experience whether it’s greater self-awareness or something learned that will serve you on your journey in finding your perfect person.”

Matchmaker Nahla Grafer suggests, “Reframe rejection. Call it redirection instead. Allow yourself to catch the next wave and flow in another direction. That feels way better than feeling sorry for yourself.”

Matchmaker Erin Soskin brings up an important point, “One hugely important thing is realizing the impact of NOT having the difficult conversations. Most people are good-hearted and don’t want to hurt someone’s feelings, so they ghost when they’re not sure how to speak up or try to “lose a guy in 10 days” when they don’t know how to express they’re not into him. I also find that many simply stay even when their heart is no longer in it.”

Being open and honest is empowering and can change others’ perspective of you for the better even if you’re not saying something they want to hear. Nahla explains, “It’s sexy to have the confidence and security to be transparent and tell the truth. Ghosting is cowardly and immature. People deserve truth and kindness; you stepping up and speaking your truth says more about you than it does them.”

Erin adds, “Get clear on what you want and need and be mindful from the very first introduction so you’re in a state of dating consciously. After a couple of dates, don’t feel bad telling someone you don’t think it’s a fit. However, if this is someone you’ve been dating and communicating with regularly tread lightly with kindness and compassion when letting them know you’re not interested in a relationship. If you’ve lost that loving feeling for someone you’re in a relationship with, be very sure the relationship is the issue before breaking things off. Sometimes stress in the workplace, a change in schedule, jealousy, family issues, etc. can cause the rift. Breaking off the romantic connection might be the right move, but before doing so be clear if this is someone you’d like to keep in your life and let them know. If not, lovingly say goodbye.”

Have you been putting off an awkward conversation? If you have questions or want advice from the Kelleher Matchmaking team, please leave a message in the comments section below. If you’ve recently been on the receiving end of bad news, pick your chin up. Your match is out there.