I’m lost in a sea of questions! I’m very out of the dating loop (haven’t been on a date in years and my last one was hardly a real date). But anyway, I have one Thursday and being that I over-analyze things like crazy and don’t know what I’m doing to begin with, I have lots of questions.
Fantastic! Let’s get to it.
what do I do if the conversation just isn’t happening?
Ideally, this should never happen because you are an observant human being capable of making conversation out of just about anything or any situation. Right? Well, if that’s not the case, then you can fall back with asking questions about her. After all, the object of a first date is to get to know another person. Alternatively, you can have a set of prefabricated lines designed to stir conversation, sort of like a modified pickup line. I prefer being more spontaneous, so I don’t have any to share with you. But there are plenty of resources out there on this sort of thing.
What about if the date is a dud and I am dropping her off, what do I say?
I hate it when that happens.

I’m a fan of movie quotes in this instance. “Good night, and good luck” is a favorite line for me. It’s simultaneously straight forward and bizarre in the context of ending a date. It has well-wishes for her future and renders the relationship doubtful enough that a woman can ponder it for as much or little as she wants. It’s my favorite bad date breakup line!
If we want a second date, how long is appropriate before the next one - is a week too long or just right or what?
No no no, absolutely not! Have a second date planned before you end your first one. You can put the date forward a week or so, because a cooling-off period is both safe and rational. But why would you want to leave your newly formed relationship hanging in limbo for that long? It only instills doubt into your lovely lady. Early on, doubt will torpedo a relationship before you ever realize it. So head it off by striking while the iron is hot – score your second date ASAP. kage_ar is absolutely right about “waiting for two days” being a bunch of Hollywood garbage, crafted by people whose dates are more fond of their money than their sparkling personalities.
Other not as important questions but things I’ve just been curious about: how many dates before kissing, holding hands, etc.? Is this something I just need to gauge based on our interest in each other?
Absolutely. There’s nothing worse than making an escalation gesture prematurely. Remember when you were in high school and you awkwardly asked The Relationship Question for the first time? “So, uh, do you wanna be my girlfriend?” It was pretty terrifying wasn’t it? When it comes to dating, if you have to ask if you’re ready for something, then you’re probably not. Be charming, be a good guy, be bold, but above all make her comfortable with being around you. When the time is right, you’ll know – and the transition be smooth as silk.
Some may construe this as advice to take things slowly. While it’s generally very good advice, it’s not necessarily the case. There are a number of cues, verbal and non-verbal, which are difficult to concisely describe but simply come with practice and study. Your mileage may vary, and I do mean
yours. In our culture, the task of driving relationships forward leans more heavily on men than women, so be aware of that. Your boldness and confidence will be the most determining factor on how quickly things escalate.
I was thinking it might not be right for several dates, but I don’t know what the general view from a Catholic perspective is.
Again, it has everything to do with you, her, and the mode with which you intend to pursue this relationship. You can make certain expectations based upon your mutual religious preferences, and these can (and should) be constructive rather than limiting. In other words, don’t try to think of Christianity as something that will keep you from doing certain things, but rather something that brings you together with a like-minded person. This is, after all, the crux of dating in any context.
Good luck!
