How to Take a Flirty Relationship to the Next Level

4 strategies help transform a flirty rapport into a deep and lasting connection.

Posted Jan 17, 2021

Prolonged eye contact, good natured teasing, and longer than usual chats may signify that someone you're interested in is also interested in you. These four strategies can then help transform a flirty rapport into a deep connection.      

First, when bumping into the person, steer the conversation from small talk to a specific and meaningful topic. Pets, children, or hobbies are often at the center of a person’s world. Asking about any of these things may open the door to a personal discussion. For example, “I never asked... do you have kids?” or “I noticed the beautiful plants in your office. Are you a gardener too?”

Second, recall a meaningful occurrence in a person’s life and ask about it. This conveys thoughtfulness and care. “How did Sally’s math test go? Last time we spoke, you were worried she’d freeze.” Once a person begins discussing something he or she loves, the conversation usually takes off. “She got an A, but we are dividing proportions tonight. Cross your fingers. Sally is funny. She is so strong in science and English, but her math weakness comes from me.”

While he or she elaborates, continue to ask open-ended questions. “That’s great. Math anxiety is the worst. Was she relieved she got through the first exam?” People usually delight in talking about topics near and dear to their hearts. Opening a dialogue about these things may be an effective way to deepen the conversation naturally.

Second, if the reply to a question about a pet, child, or hobby is negative, listen for a feeling and reflect the feeling. For example, Shelly recalls Tim excusing himself from a meeting because his cat was ill, so she asks about the cat when she sees Tim at the gym. To her surprise, his face falls and he says, “I had to put Tiger down yesterday. He had a heart condition.” Shelly replies, “Tim, I am so sorry. How are you doing?” Tim recounts the sudden and difficult decision to put Tiger to sleep.

As he is talking, Shelly listens for feelings and honors them. “You must be shocked and devastated. It happened so fast. It must have been difficult.” Tim senses Shelly understands and continues to open up. “I did everything I could to help him, but nothing worked. He deteriorated quickly. One minute we were playing and the next, he could barely move. I did not know what to do.” Again, Shelly focuses on his feelings and says, “I bet you felt helpless and alone. I am so sorry.”

As a result of Shelly’s empathy, Tim feels understood, supported, and less alone. Shelly conveys a sincere understanding of Tim’s emotional state. She gets it. Tim realizes his emotions are safe with Shelly and remains open with her. The relationship grows stronger.

When listening for a feeling, often a person worries about getting it wrong. For example, perhaps Tim was relieved that Tiger passed away. It was an end to his suffering. Shelly, however, misinterprets his feelings and reflects on shock and devastation. Although she missed the mark, this provides Tim with an opportunity to look inward and clarify what he is feeling. Tim says, “Actually, I’m less devastated and more relieved. I’m thankful Tiger isn’t suffering any longer.” Now, Shelly is able to reflect and validate the identified feelings. “I get it. You are comforted that he is out of agony and at peace. I would be too.”

Third, after fully listening and supporting him or her, try to remember a similar experience. Embrace an opportunity to mention it during the next encounter. “I am glad you are feeling better about Tiger. What a tough experience. I had a similar experience with my dog, Charlie.”

Tim has an opportunity to reciprocate the empathy which creates additional closeness in the relationship. Sharing a difficult experience often creates a bond. If Tim is unable to empathize with Shelly and fails to acknowledge her experience, she may think twice about initiating a relationship with Tim. He may lack empathy.

Fourth, say the person’s name frequently during the conversation. “Anne! I am so happy to see you. I thought you despised breakfast food. How have you been, Anne? It’s nice to bump into you.” Saying a person’s name validates his or her importance to you. Sneaking it in may convey strong and positive regard. If a worry exists about sounding silly, try saying the person’s name during a greeting and a goodbye. For example, “Hi, Rick, how are you?” “See you at tennis, Lisa.”

Much of falling in love involves growing close to someone. Feeling understood, known, valued, and respected, not only for achievements, but for who a person is, allows an individual to truly trust another. Being loved and cherished for both attributes and flaws validates a person and allows a person to feel like he or she is anything but alone in the world. This can be comforting, reassuring, exciting, and fun.

Accelerate the process of getting to know someone. Focus on what is meaningful to them and learn more about these things. Empathize by listening and honoring the person's feelings, and convey respect and affection by referring to him or her by name. These techniques may break up superficial small talk and deepen the dialogue. Opening up and finding shared meaning may also solidify the relationship.