The 5 Questions to Ask When You're Meeting Your Girlfriend's New Man

I pulled up to the restaurant and sat in my car for a moment. I couldn’t believe that I was actually nervous! One of my best girlfriends, Angelina, had been talking about Charlie for a few weeks now. They had shared incredible dates, developed significant feelings for one another and now it was time for him to be introduced to the girlfriends. Enter left stage: Me nervous in my car. This was one of my dearest girlfriends – a woman with whom I had shared really good relationships stories as well as the really bad ones. We want nothing more than for our girlfriends to experience the wonderful love they deserve, right?

Meeting your girlfriend’s new man is a treasured and serious responsibility! In all of her vulnerable beauty, your girlfriend is basically handing you her newfound potential for love and seeing what you have to say about him. So what do you do? How do you handle such an honor with respect, honesty and love? You make sure to ask the right questions that will enable you, the trusted girlfriend, to not only get a good idea of who this guy is and why he deserves to share the company of your phenomenal friend, but also a chance to represent yourself as the caring, amazing girlfriend that you are.

*One Very Important thing to keep in mind as you’re asking these questions: your job is not to judge him for his answers. Your job is to simply let his answers paint a picture of who this man is and how he might mesh with your girlfriend.

Question 1: “What do you enjoy doing?”

You already know that your girlfriend has gone through his extracurricular activities and made sure some of them line up with her own. However, asking this question enables you to experience how he talks about what he likes to do. Why is this important? Because when someone loves something and is passionate about it, their eyes light up, they show excitement and they become a little more animated. When Charlie told me how much he loved to mountain bike, three things became clear to me:

1.He enjoyed athletics. So does Angelina - Check.
2.He loved spending time with his friends doing this activity. He has friends and spends quality time with them – Check.
3.He is adventurous and has hobbies outside of work – Check.

Question 2: “How did you two meet?”

I know you’ve already heard this story from your girlfriend…probably a few times. But asking the new guy his version of the story is always interesting and fun. As he’s telling the story, pay attention to a few important details:

1.Does he touch her while he’s telling the story? When light touches are exchanged, they usually signify unity and togetherness. If he reaches for her hand or softly grazes his hand on her leg, he’s appreciative and grateful for the union.
2.Is he enjoying telling the story? If he seems annoyed by this question or doesn’t have any excitement telling the story, he’s probably less excited about your girlfriend than she is about him.

Question 3: “What do you do for work?”

I know, a boring, airplane-type question. However, our careers tend to be a huge part of our lives. Asking him about what he does gives you an opportunity to see him in his element. Ask follow up questions about the specifics of job and genuinely listen to where the conversation takes you. Observing him explain his career will be incredibly interesting and will also reveal a lot about his character. When Charlie said that he managed a sales team for a tire company, I was interested. He went on to explain about how he got to that position, what his management style was and what he liked best about his company and its products. The explanation gave away a lot about Charlie’s ability to interact with and lead others, his work ethic and his desire to grow professionally. It was also a great conversation starter about the tire issues I had been having lately!

Question 4: “Does your family live here too?”

Simply an opener to begin discussing his family. You will either get a yes, to which you can follow up with a “so do you get to see each other often?” or “how many of you are there?” Or you will get a no, in which case other questions can follow about where they are, how often they see one another, etc. By asking questions about your girlfriend’s new man’s family, you can get an intimate glance into his family dynamics. Let’s be honest – we’ve all grown up with some sort of “dysfunctional” family norms. However, if you know that your girlfriend really wants someone who has come from a good family, or who has good family values or has good relationships with their parents and siblings, then this question will allow you to see those traits. Charlie excitedly told me about his parents who were coming to visit that particular weekend from the city where they lived a few hours away. It was apparent he got along with his parents and I knew that was an important element for Angelina. Let’s say the guy isn’t so excited to talk about his family or doesn’t seem to have many good things to say about them, it’s not necessarily an immediate red flag (see definition below), it’s simply something to note.

Question 5: “If you could go anywhere tomorrow, where would you go?”

The random questions are not always well received, but they are very powerful, so it’s important that you get one in. Do it in a way that is non-threatening, like telling him that your work associate asked you this question today and you were thinking about it and you would like to go to Italy. Where would he like to go? The random, off-the-wall questions are important because they show creativity, an ability to think on the spot, and ultimately, they reveal a lot about the nature of his heart. If he immediately lights up and spouts out 10 different places, complete with a travel itinerary, and you can see the free spirited nature in his eyes, you will know how much he loves to travel and that he’s an adventurous guy. If this meshes with your girlfriend’s personality – great. If not, it may be an interesting contrast. If he takes a long time to answer, seems unnerved by the question (how dare you ask him something non concrete!) and the only answer he can come up with is “the beach,” then he’s probably not Mr. Adventure. Again, this is not to be judged…simply put into the matrix that is the co-existence of him and your girlfriend.

Meeting your girlfriend’s new man is not a task to be taken lightly. It’s an art of walking the fine line between supporting your friend and creating conversation that will highlight his character. Entering the situation with the proper questions, however, will make this endeavor easy and very enlightening!