I Don't Hold Back on Asking Questions!

Dr. Robert Wallace
Fri, 13 Mar 2026 21:00:00 -0700
Lifestyle

DR. WALLACE: I'm a female college student, and I enjoy going out on dates with new guys, but I'll readily admit that very few of them make it past a second date with me! The reason for this rest entirely with me: I tend to ask guys a lot of questions.

On the first date, I'll stay calm, ask a few general questions and try to focus on the conversation and getting a feel for the guy, his personality, how he handles himself and how he interacts with me.

Then when a guy and I go out on a second date, I have a strategy where I tell him intermittently through the evening or afternoon various experiences I've had in the past, things I do, things I enjoy, perhaps things about my family and so forth. Then after I volunteer this information, I'll ask an open-ended question of the guy about the same topic and what his past experiences have been. Most guys will answer these questions, but I will say that sometimes one out of four will shut me down or say they're not comfortable sharing direct information with me about their family background, for example, on a second date.
Updated: Sat Mar 14, 2026

DR. WALLACE: I'm a female college student, and I enjoy going out on dates with new guys, but I'll readily admit that very few of them make it past a second date with me! The reason for this rest entirely with me: I tend to ask guys a lot of questions.

On the first date, I'll stay calm, ask a few general questions and try to focus on the conversation and getting a feel for the guy, his personality, how he handles himself and how he interacts with me.

Then when a guy and I go out on a second date, I have a strategy where I tell him intermittently through the evening or afternoon various experiences I've had in the past, things I do, things I enjoy, perhaps things about my family and so forth. Then after I volunteer this information, I'll ask an open-ended question of the guy about the same topic and what his past experiences have been. Most guys will answer these questions, but I will say that sometimes one out of four will shut me down or say they're not comfortable sharing direct information with me about their family background, for example, on a second date.

Those who do answer the questions — and I have a lot of questions — often "disqualify" themselves by something they've said, as sometimes the answers sound insincere.

My girlfriends think I'm extremely unwise to be such an information gatherer that early when dating someone new. They tell me that from their experience, it's better to focus on the two personalities and current topics rather than trying to gather specific information about the person, past history, family and so forth.

I've listened to my girlfriends and considered what they've told me, but the last two times I've dated new guys I've reverted to my usual style, meaning I let the questions fly! Do you think I'm making a mistake by doing this? — I Ask a Lot of Questions, via email

I ASK A LOT OF QUESTIONS: On the one hand, I always believe in a person being true to themselves, but on the other hand, I haven't been able to witness your line of questioning, the tone and inflection you are using, and the specific requests for information you are soliciting.

You don't necessarily want to come off as a defense attorney or a prosecutor interviewing a witness in court! It would be far better for you to adopt a style similar to someone doing a radio interview with a musician, for example. We've all heard those types of interviews where various questions are asked and answered in a casual, free-flowing conversation.

The one benefit I can see to the way you operate is that you weed out your dating possibilities quite efficiently within two dates. If someone is going to be incompatible for you in the long run, I do agree it's better to find that out as soon as possible. But make sure to check your tone and the way you ask questions, and try to do it more in a "friendly interview" style if possible, but by all means stay true to yourself and your personal style.

HIS SCHEDULE MOVES AROUND, AND I'M EXPECTED TO BE FLEXIBLE

DR. WALLACE: My boyfriend of three months is a great guy for the most part, but he has a few habits that aren't so compatible with me. For example, he regularly inconveniences me by moving around the times of our dates because of some fluctuation in his personal schedule. Alternatively, if he doesn't actually set a day and time for our next date, he will tell me that we'll go out "within the next few days," but then he'll keep me guessing until he finally asks me out on relatively short notice, sometimes only an hour or two beforehand!

I will admit he's pretty popular in our school, so I am benefiting from a huge dollop of social currency by dating him. All my girlfriends think I'm very lucky, and my circle of friends has literally doubled since I've been dating him. What advice do you have for me at this point? Should I say anything or just accept his ever-moving and inconsistent schedule? — I'm Expected to Remain Flexible, via email

I'M EXPECTED TO REMAIN FLEXIBLE: The first thing that jumps out at me is that you used the phrase "social currency" regarding dating him, as you are likely indicating that it makes you look good in front of your friends and a growing circle of friends you've met that has expanded no doubt because you've met a lot of his friends as well.

Yes, it can be frustrating to deal with someone who is tough to pin down on the schedule, but the bigger issue in my view is how the two of you get along once you're together. How much fun and togetherness do you have, and how does he treat you one-on-one? If all that is good, focus more on your relationship and less on thinking about any social currency.

Regarding his schedule, sometimes the best way to combat a free-flowing schedule by a partner is to become magically unavailable when asked to do something on very short notice! Simply explain that had you known, you would've kept that time open, but you've made another commitment to go shopping with your family or some other reasonable thing that you are actually going to do with that time.

Then explain later that you're more than happy to schedule with him in advance, and stick to it as long as he can give you more advance notice on a regular basis.