Dating and Relationship Advice

Imagine you're on a dating app. You start chatting with a man you matched with, and begin developing feelings for him. Then, smack dab out of the blue, the conversation starts dragging. What can you do? How can you grab his attention and get the messages flowing again?

Alexandra Stockwell MD, Relationship and Intimacy Expert and bestselling author of Uncompromising Intimacy told me, “The best way to keep the messages flowing is to ask questions. Be curious and ask what you want to know, and then ask follow up questions to deepen the conversation.”

Questions That Lead to Follow Up Questions

When you’re asking a question that leads to a follow up question, you’re encouraging a better stream of communication. When you ask your potential SO, “how was your day?” and he responds, “pretty good,” you might not know the best way to respond because you asked a dead-end question.

Dr. Stockwell provided me with three better questions to ask:

  • What were you thinking about when you woke up this morning?
  • What was the last book you read?
  • What was your favorite class in college?

These questions come with a set of follow up questions. For instance, when he tells you the name of the last book he read, you can ask what it was about, and what his favorite parts were. This beats asking another dead-end question, such as “do you enjoy reading?”

What Should You Do When The Convo Stops?

Nothing sucks more than a great conversation coming to a complete halt—especially after you start bonding and discussing plans for meeting up in real life. What is the best way to approach this dilemma and when do you give up and move on?

“The fact is that we never know what is going on in such a situation. Did he have some kind of personal or familial emergency? Is he unexpectedly busy? Is he married and misrepresenting himself? Is he no longer interested? There is no way you can find out the truth—the key is to keep an open mind and not let your insecurities take over,” Dr. Stockwell said.

I know from personal experience how easy it is for my insecurities to get the better of me. Even when I’m in a committed relationship, I’ll occasionally worry when my boyfriend doesn’t promptly respond to one of my text messages. When this happens, I wonder if I did or said something wrong.

“In this situation, the best thing you can do is wait a few days, and then send a warm message (without resentment or blame) saying, 'I really enjoyed our conversation and am interested in continuing talking. If you feel differently, I wish you all the best and hope you find what you are looking for.'

If there is no response, you still don’t know what led to the lack of contact, but you do know that it’s time to let it go. If he was busy, or there is some other circumstance that has nothing to do with you and he is still interested, he will respond and you two can pick up where you left off,” Dr. Stockwell continued.

How Can You Revive a Boring Conversation?

When you’re talking to someone new on a dating app, there are bound to be times when the convo gets dull and repetitive. Rather than running away and finding a new match, you can attempt to revive the conversation first.

Dr. Stockwell said that there are two effective ways for you to nudge the conversation, so it can effortlessly flow once again. You can ask unexpected questions, even when they have nothing to do with the previous messages you sent. Additionally, you can let your vulnerability shine while asking heartfelt questions.

“Give yourself permission to be outrageous, and be prepared to share your own answers, too,” she said.

For example:

  • What breakfast food did you enjoy when you were a child?
  • Have you ever ridden horses?
  • If you could have dinner with anyone, at any time in history, who would you choose?

There’s no reason for you to feel embarrassed asking questions that some people might consider silly. You’re exploring your options and learning everything you can about the person you’re talking to every day.

Dr. Stockwell explained the importance of phrasing. You could say “I watched a movie last night and went to bed early,” but you’re not really bearing vulnerability there.

Instead, she suggested saying “I watched a movie last night and it really touched me. This one scene reminded me of a time in my life when I really needed to figure out what was important to me.”

Then you can share a little bit about what you experienced in life and why the movie brought those memories to the surface.

“The key is to pivot from a boring conversation into one that is more meaningful. There’s no need to be flashy—just bring more meaning to the exchange, and if you are a good match, your chats will naturally become more interesting for both of you,” Dr. Stockwell said.

More Questions You Can Ask

There’s no shortage of questions you can ask when the conversation slows down. Nevertheless, we all have our moments when we struggle with asking the “right question.” But there aren't right or wrong questions—so long as you’re genuinely curious.

Dr. Stockwell left us with some final questions that will help keep the messages flowing:

  • Do you enjoy what you do for a living?
  • When you were in high school, is this the job you hoped for?
  • Do you get along with your coworkers?
  • What do you love most about your job?
  • When you head home from work at the end of the day, do you let everything go or do you continue thinking about it?

“These questions can potentially reveal who he is as a person, and help you discover whether or not you want to spend more time with him,” she said.

Next time your convo loses momentum, remember the wise words of Alexandra Stockwell MD, the Relationship and Intimacy expert—be outrageous, send meaningful responses, express vulnerability, and remember there's no such thing as right or wrong questions.