Questions To Ask Before a First Date


As you’re going through the dating process, you should ask yourself “how valuable is my time”? I’m assuming you want to find your sweetheart quickly without wasting time or suffering heartbreak. Right?


I don’t believe in wasting valuable time going on dates with the wrong people when you can screen out men who aren’t available or who aren't looking for the kind of relationship you want with a simple phone call or video chat.


These are key questions you can ask that will help you identify obvious deal breakers or red flags before wasting the time, energy and expense to go on a date with them. I recommend asking these questions on a phone/video conversation, before you agree to go on a first date with anyone you’ve met online or who’s a stranger to you.


Ask about his marital or relationship status:

Does he have a girlfriend? Is he currently seeing someone? Is he married or currently separated? Unfortunately, many men on dating apps are married. Some sources quote that half of men on dating apps are married. As a high-quality woman who is ready for the love of her life, you want to quickly identify the married men and pass on those guys.


Separated and recently divorced guys are also not in the emotional/mental place you are in and they likely have some work to do on themselves before they’re relationship ready. Some of the men who aren’t over their last relationship will show obvious signs that they haven’t emotionally moved on yet, but others won’t show those signs until later in a relationship after you’ve already invested a lot of your time and emotions in them.


The obvious signs that someone is not over their ex are when they get upset, sad or angry when they talk about their ex or they talk about them often. They might speak in unflattering, unkind, condescending, degrading or defamatory ways about their ex. No matter how long it’s been since their break-up, this person has not sufficiently processed the emotional fallout yet and you shouldn’t put yourself in the position to be their muse, distraction, entertainment, rebound person, therapist, pen pal or sounding board.


If someone is separated, I also don’t advise meeting them in person because this is a person who is still married to someone else and is not free for a committed relationship with you. This should be a deal breaker right off the bat. No matter what they say or how soon they expect to be divorced, they’re not free until the divorce decree is signed, some time has passed and they’ve done personal growth work. They’re simply not free and clear of their last relationship nor are they emotionally available for a long-term relationship. I speak to women who feel they must seize the opportunity to get in there with a separated man before any other woman claims the guy. For a high quality self-valuing woman, this is a hard NO. It’s a recipe for heartache.


A man who is recently widowed should also be a hard NO for you. I made that mistake two decades ago myself. I went on a date with a man who had lost his wife 3 months prior to the date. Before I knew it, I became his therapist and ended up missing many red flags. Most importantly, he had not grieved the loss of his wife and should have had a mourning period before dating anyone. In his case, he needed a fair amount of therapy to deal with her death as well as issues that were already present in his life before his wife passed away. I did not have the wisdom back then to avoid dating or getting into a relationship with someone in his situation.


Ask him what he is looking for in a romantic relationship so you can determine if you’re on the same page with him. If he’s on a dating site or asking you out in the Starbucks line, then you should ask him right off the bat what he’s looking for. The right man will not balk at this question. A decent man will be willing to answer it and reveal his intentions. A lot of men will tell you that they’re either looking for something casual/laid back, easy going, or that they’re hoping to find their special person for a relationship or that they are looking for a friendship that could develop into a long-term relationship. They will be direct and answer the question. Would you want someone who isn’t direct and open to answering this question?


If their dating profile says they’re looking for something “casual” or they “don’t know yet” if they want a relationship, believe what they’re saying and swipe left on those guys. The men who are ready for a relationship and don’t need to be convinced to be ready will say that on their profile and they’ll be open to being asked this question because they also want to make sure they’re meeting women who are on the same page as them and don’t want to waste their time. There are ways to ask the question without seeming to be looking for a relationship with them specifically. Be prepared to answer this same question. You’ll want to say something along the lines that “you’re ultimately looking for a long-term committed relationship and will take the time needed to ensure you find that right person”. That way they will understand that you’re not looking to fit them into that role or start an instant relationship. You want to communicate that you’re looking for a compatible match, however long that takes for you to find.


Ask yourself if this person is speaking in a way that is abusive, angry, condescending, derogatory, dismissive, very negative, controlling, pushy, sexually suggestive or unkind towards you or other people”. You might notice this in how they speak about others in their life such as family, their ex, their children or people at work, or how they interact with others such as staff at a restaurant or store clerks.


Does he show a lack of empathy or compassion when you bring up topics about yourself or others where empathy and compassion should be shown? It may seem like a given that others will show compassion when you mention for example, that your father is very ill or your pet just died, but you will be surprised and shocked to notice how many men (and women) don’t react at all to this with any empathy and don’t bring up a time when they felt as you do to demonstrate they understand and have compassion for what you might be feeling.


One of my friends expressed to me how she talked about her health concerns to her husband and he had no reaction at all. He showed no concern for her or concern to help and support her to address this concern. In that marriage, he was concerned only for how she would meet his needs and was not emotionally available or emotionally understanding of her needs. A thoughtful, caring and kind man will jump in to offer anything he can do to help you resolve any concern and to protect you from pain or harm.


Does he live out of town or in a different state? This is not always a deal breaker but initially, I don’t recommend setting your dating app search for men who live out of town. Of course, it depends on where you live. For you, this may mean that you initially don’t consider people who live more than a 1-hour drive from you. However, if you live in places like California where people routinely travel great distances through lots of traffic, you may need to set your geographic range to a 1½ hour drive. While some long-distance relationships do work out, most of them do not. You can always expand your search to a larger area if needed.


Is there very little or no information on his profile? Even if he’s a celebrity, if he’s truly looking for a relationship there is no reason why his profile would have no information in it. In fact, I’ve run across celebrities online and they share quite a bit about themselves. For example, is the town he lives in missing from his profile? This is something you might see on Bumble a lot. Many men purposefully avoid including the town they live in because they’re using the app for hook-ups or they live out of town and are looking for a hookup.


A friend recently told me the guy she had started dating said he lived in Chicago on his dating profile but she eventually found out that he really lived 3 hours away! He would avoid answering the question about where he lived. Finally, she discovered he didn’t live in Chicago at all! Information that is intentionally withheld is basically being deceitful. The information you notice is only the tip of the iceberg for other key information that is being withheld.


Does he clearly state his relationship goal on the app or did he leave this question blank? Many men leave this question unanswered. Please swipe left on these profiles. They’re not looking for a relationship. Otherwise. they would have said so. If they’re divorced, their profile should specify that they’re divorced. Otherwise, if their relationship status is not mentioned, you’re going to need to confirm that detail on the phone with them.


These are just a few things to look for and discuss before agreeing to meet someone in person. A client recently shared that she asked to speak to a man by phone or video chat before meeting him in person. His response wat that he doesn’t give out his phone number and will only meet in person because it’s the only way he can determine “if there’s really a connection”. There were a couple of other shady things about him, such as he didn’t indicate where he lived on his profile. She was tempted to meet him because he was quite handsome and she hadn’t seen anyone online in weeks that she wanted to meet. However, the chances this man was married or had some other significant issues, like being controlling or paranoid, were very high. She told him that for personal safety reasons, she never meets strangers without having a phone call with them first. Then she unmatched with him on Bumble. She saved herself the 2 hours she might have wasted to meet him for a date. She trusted her instincts about this situation. You have to trust your instincts!


So what questions do you ask men before meeting them in person?

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