The beginning stages of dating can feel like a mini version of Groundhog Day; first dates that go nowhere and prolonged “talking” stages that take up hours of your time but don’t actually lead to a relationship. The beginning stages of dating, however, are crucial because that is where first impressions are made. How you present yourself during those first encounters (via text, phone call, or in-person date) determines whether that person will want to see you again – eventually breaking the Groundhog Day dating cycle.
For those of us still fighting in the trenches of modern dating, these interpersonal situations require us to be self-reflective and self-aware. We have to ask ourselves, “How am I coming across to my date?” Sometimes the other person loses interest for their own reasons, but sometimes it’s our own lack of effort, intentionality, and impressiveness that puts the nail in the coffin.
And listen, I’ve been on both sides of the equation.
As someone who struggles with timeliness, I’ve been late to dates and had to change my habits to make a better first impression. I’ve also been on the receiving end of unimpressive behavior.
So if you’re a guy who’s asking himself, “What went wrong? Why doesn’t she want another date?”, here are a few tips for making a good impression with the women you’re pursuing.
Stop Chatting, Just Ask Her Out
Let’s start at the beginning. Impressing a woman begins with your first encounter. In 2024, most relationships start online – someone slides into your DMs on Instagram, messages you on a dating app, or friends you on Facebook. Once contact has been made and the interest is mutual, be proactive. Don’t keep it online.
If you’re messaging back and forth with a woman online for longer than two days, she is most likely thinking: “Just call me!” or “Just ask me out!” If we’re chatting with you, it means we’re interested. If we’re asking you questions and continuing the conversation online, it means we like you. It’s up to you to take the conversation offline!
As women, we want to follow the man’s lead and respond to his pursuit of us. If you aren’t actively taking the conversation to the next level and asking us out, we’re going to assume you’re not actually interested and we will reflect that disinterest and stop communicating.
Be On Time, Even For Phone Calls
We all know the progression of online dating. First, you chat within the app, then you exchange phone numbers to text, and then you schedule a phone call. A phone call might not seem like a big deal, but really, it's a virtual first date. Treat your phone dates like they’re a first in-person date. As women, we are evaluating that first phone call or FaceTime the same way we would a first date.
That first phone call is where we get a tangible understanding of your actual personality, character, and behavior.
One guy I dated from CatholicMatch rescheduled our phone dates nearly every week because his friends frequently made last-minute plans. To me, this communicated that developing a romantic relationship wasn’t a priority to him and that his friends would always win when it came to his attention. More recently, a guy was 45 minutes late to our first phone date – so I just thought I was being stood up! Both of these men exhibited behavior that made me think, “If he’s like this when the bar of commitment is so low, what would he actually be like in a relationship?”
Be the man who sticks to his word and arrives when he said he would! Show that you respect the time of the woman you’re pursuing.
Ask Her Questions (And Be Genuinely Interested)
My number one reason for a lack-luster first date is a man with poor conversation skills. In fact, this is somewhat of an epidemic in dating as more and more women have complained about having to carry the entire conversation on dates. I’ve left many first dates saying, “I don’t think he asked me one question.” I’ve also left space for plenty of awkward silences, giving the man the opportunity to lead the conversation – it usually leads to crickets.
Asking your date questions about themselves conveys a basic level of interest, and it’s a socially polite way to keep the conversation equal, rather than burdening one person with the job of keeping it going. Again, self-awareness is crucial when dating! Always ask yourself, “Am I keeping up my end of the conversation?”
Remember, in the heart of every person is the desire to be known and understood.
When it comes to marriage, we all want to marry someone who we find infinitely interesting and exciting. If you are on a first date and not asking any questions, it conveys that you don’t find them interesting. So ask questions! Be creative! Don’t just piggy-back off of their questions and say, “what about you?” Reflect on who this person is – their history, passions, opinions, and goals. What about them is inspiring to you? Surprising? Or fascinating? Learn about who they are.
Dress With Intention
As Catholics, we believe we are a body/soul unity. How we physically express ourselves is a manifestation of the internal. It reveals how we see ourselves and how we view others – this is an important form of non-verbal communication. I once went on a first date with a man who wore a zip-up hoodie and sneakers. It made the impression that he didn’t really view the date as a date. I thought, “He’s not really taking dating seriously.” The way he dressed expressed a lack of intentionality and self-care, which was later confirmed by his actions.
When you put in the effort and dress well for a date, it’s not only a positive reflection of how you see yourself (worthy of dressing well), but it’s also a compliment to your date.
When you show up in a sharp outfit, it communicates to your date that you see her as worth getting dressed up for. It communicates that you think highly of her and want to impress her. As women, this makes us feel respected and like you’re just as excited as we are about the date!
Set Up The Next Date
Nothing is more attractive than a man who knows what he wants and clearly communicates that.
If you enjoyed the date and want to go out on another – say it at the end of your date! Don’t be afraid! When you set up the next date, it shows that you have confidence and that you know yourself and what you want. Our culture is plagued by wishy-washy intentions and guys who “aren’t sure” and who lead women on. Most of the women you encounter will have been burned by those kinds of guys.
Be different from the other guys and communicate what you want! I know what you’re thinking, “But what if she says no?” Then at least you were the guy who was clear and confident – the guy who had character.
In Conclusion…
Dating can be daunting, especially for the men who are expected to pursue and lead. As Catholics, sometimes we self-sabotage in dating because we’re not sure if we’re ready for marriage or if marriage simply seems scary. Sometimes a man will try to manage the woman's expectations by lacking intentionality, as if to give himself a trap door in case things get too hard.
It might seem easier leaving a woman you’ve already disappointed over and over again, but really it just turns you into someone you don’t want to be.
The biggest way to impress a woman is to be a man who knows himself and always says “yes” to the right thing, even if it’s the hard thing.
This type of commitment to virtue will be evident in your character, and trust me, the right kind of woman will admire that more than anything.
