4 Little Questions Dating Experts Wish You’d Ask Before Dating Anyone

What you need to ask yourself to make sure you like him.

guy and girl on date chatting Supavadee butradee / Shutterstock

Trying to think of good questions to ask a guy when you’re on a date? You want to come across as cool, witty, easy-breezy and laid back, but also an intelligent person who has her stuff together. I get it, it’s like walking a tightrope. Even if you achieve the death-defying walk across, what if you don’t like what’s on the other side of the table? It’s not just about him liking you or thinking you’re as funny as Amy Schumer, it’s also about you liking him.  


This may be radical thinking, I know. When dating, we tend to only think (a.k.a. obsess) about how we're perceived. We want to believe we have control over that by what we wear, what we say, or the looks we give (read: we don't). Did you ever stop to think that your date has the same concerns and anxieties? Dating is difficult when you're serious about finding a person with a long-term relationship. Rather than overthinking everything about who you are and what you do, it's important to shift some of that focus to how you feel about him. So, here is the real issue: How do you know if he will make a great boyfriend? What do you need to ask yourself when dating a guy for the first time?


RELATED: 3 Tiny Signs He Wants To Be With You For The Long-Run

Here are 4 little questions dating experts wish you’d ask before dating anyone:

1. "How do I feel when I’m with him?"

This takes some introspection, presence, and awareness. Do you feel honored and respected? Do you feel heard or does he do all the talking? Does he ask sensical and interesting follow-up questions? Is it difficult to carry on the conversation or does it flow pretty naturally like you’re talking to a good friend? If you’re sitting there wondering if you should play a party game on your phone to get him to engage with you, that’s probably not a good sign. 



After a few dates, consider if you feel like a good version of yourself around him. Do you feel that he brings out the sparkling parts of your personality or do you make snarky comments to yourself as you try not to roll your eyes? After a few more dates, think about if you trust yourself when you’re with him. 


Do you do things you wouldn't ordinarily do because you want him to like you or you feel you should? Are you more impulsive than usual or more guarded than usual? These behaviors may become apparent before you are in touch with the reason why you’re betraying your true self. It’s imperative to be mindful of this drift from your "normal" self so you have time to swim back to shore versus needing rescue when you’re in too deep.  

RELATED: 15 Relationship Red Flags You Should Never, Ever Ignore

2. "How do his behaviors reflect on his character?"

This is where you’re going to examine how trustworthy he is. Does he do what he says he is going to do, as in: is he dependable? Dependability and reliability seem like two sides of the same coin and they are related. Adventurousness and spontaneity are great at certain times, but if you’re looking for a serious relationship, you want to know if you can depend on your partner when you need him. Does he call or text when he says he will?  How does he act around strangers? Is he courteous, polite, and respectful? Many people reference how people treat wait staff at a restaurant, janitorial staff, or service people.  

If you want to be with someone who cares about others besides himself, these are important interactions to observe. Steve Harvey references three characteristics in his book, Act Like a Lady, Think Like a Man, where he suggests men are interested in you if they profess how they feel, they look to protect you from harm, and they exhibit behaviors suggesting they want to provide for you or ensure that you have what you need.


RELATED: 10 Signs Of A Good Man To Look For In A Guy

3. "What are his relationships like with others?"

Does he have close relationships with friends and family? Can he engage in conversation with your friends and family when he meets them? If not, is he just introverted, or is he disengaged in a way that is rude or inappropriate? Introversion is something that can be worked on as he becomes more familiar with your friends and family and understands how he may prefer to interact (in smaller groups, or just one on one, for example).



4. "How do resolve conflict?"

How does he handle conflict or disagreements with you and with others? Does he hold things in until he is ready to explode? Does he disappear or give you the silent treatment?  How does he respond to you if you express discontent? Is he able to listen and acknowledge your perspective without blaming you for your feelings? 


Mature communication about unmet needs or expectations is a vital ingredient to building a strong foundation for your relationship. Considering these categories of questions when dating will draw your attention to the factors that can affect the long-term health of your relationship, long after the initial honeymoon period fades.

RELATED: 6 Key Signs He Is Serious Boyfriend Material

Anya Surnitsky is a licensed clinical social worker and a Certified Daring Way™ Facilitator. She has been featured in PsychCentral, the Unapologetically Sensitive podcast, TherapyDen, and more.