First Date set for 2 weeks from now. How do I keep her interest?


imsleepin asks:

So I met this girl online the other day, using a dating app (but not tinder), and we really hit it off. I asked when she was free to go on a date and she told me she’s out-of-town, but gave me her number and said to text her and we could plan something.

Obviously, I started texting her immediately to plan a date only to find out she out-of-town for the next two weeks on vacation. We ended up nailing down a tentative day, but she said she wants to wait until she’s back to make firm plans.

We’ve texted a fair bit since then, but I don’t want to drag a conversation on over text. I also don’t want to have a potential date fizzle out because of too little or too much texting before an actual in person meeting. So I’m not really sure how to handle this situation, especially since I’m terrible at flirting particularly over text.

Demetrius says:

I feel like I used to see these sort of questions more often, but I guess that’s just a sign of the times. This is just my own perspective and it could be wrong, but it seems like most people meet within the first week or so of messaging. Anyway, how the hell do you keep someone’s interest if you’ve planned the date but it’s a week or two (or a few) away?

First, some basics for anyone in a similar situation. Let’s say that you’re about 7 days or more from actually going on your date. The basic philosophy you want to embrace here in terms of staying in contact is to stay present, but try not to be a bother. The easiest way to do that is by reciprocating the contacts you get, so you aren’t reaching out when your contact isn’t wanted. If you’ve already planned a date and the other person texts you on a fairly regular basis, reciprocate their texting frequency. If they don’t text you post date-planning, don’t flood them with texts. Oh and never send back-to-back messages that are not about the same subject. I’m not saying you can’t send two texts (or more) back-to-back because you can, but they can only be about the same subject. Here’s an example: if you’re texting someone about their favorite bar, you can send back-to-back messages (i.e. text #1 – I’ve been to of that place, it’s really cool. text #2 – Do you know Mitch, the bartender who works there?), but you can only change the subject once you get a response. A bad example would be asking if they’ve been to a certain bar, but then following it up, without having them respond to your first question, by asking about something completely different, like their opinions Symbolist Art. Basically, treat texting like a conversation you’d have in person. Would you keep asking someone questions about different questions if they didn’t answer your last dialogue prompts? No, you’d wait for them to respond. If they don’t really text much between date planning and the actual date, you can be safe in sending one, if not both of the following texts: First, the confirmation text. The day before, send a text to confirm your date. The second is a “maybe I should send this, it’s up to me to decide” text, which you can maybe send in the following scenario (or similar scenarios): if the time between your date is 2 weeks or greater, send a text about a week or so before your date as sort of a “Hey, looking forward to meeting you next week” text. This text is both a reminder of your date, a chance for them to cancel/reschedule a week or so out from the date, and/or a way for you to gauge if they’re still in interested at all. Pro tip: If they never respond to that text, don’t expect to go on your date. Even, if there isn’t a lot of back and forth before your date, you should absolutely send a confirmation text the day before said date. That goes for everybody. Confirming a date at least the day before the date is just a good dating best-practice.

Now, let’s get more specific. In your scenario, where the reason why you’re meeting two weeks out is because of a vacation, you should probably only stick to sending the confirmation text the day before your date. If the scenario was a little different, if she couldn’t meet just because she’s really busy over the next two weeks for example, you might want to initiate a conversations or two, but because she’ll be on vacation, the “present, but not a bother” thing is especially important. Personally, when I’m on vacation, I like to escape the real world a bit, and the thing I don’t want to be doing is texting a relative stranger.  I know I just said “if your date is 2 weeks or greater, you can send a text about a week or so before your date as sort of as a ‘Hey, looking forward to meeting you next week'” but in this case, it’s probably just best to avoid sending that text. Mostly because, as charming as I’m sure you are, she’s on vacation and probably doesn’t want to be bothered. Also, because while your date is tentatively scheduled, sending a “looking forward to meeting you” text is likely to come off as less like “Oh he’s sweet” and more like “He’s pressuring me to nail down a date”. That said, all this advice goes out of the window if she remains in contact with you while she’s on vacation. If she’s texting you over the next two weeks, follow my first piece of advice and reciprocate, and disregard the rest 😊.

Now, let me just close by saying that it’s entirely possible she’ll lose interest regardless of how good you are at your attempts to keep her engaged. People suddenly and unexpectedly losing interest is just a risk you take in dating in general, and even if you do all the things above, she could still lose interest for a lot of reasons. It could be that she can’t nail down a set date because she’s got other suitors in the mix and you’re Plan Z. Or, she could be on the fence about meeting you to begin with and wants to decide post vacation. Or something completely different. Point is, you can try your hardest, do everything right, and still miss out on a date because the other party just loses interest. It’s happened to me more times than I can count, so if it does happen to you even if you do all of the above, don’t beat yourself up about it.

Good Luck Out There.


2 thoughts on “First Date set for 2 weeks from now. How do I keep her interest?

  1. I like this question because I’m really big on momentum in the dating world. If I match with someone and we can’t hang for a week or two for whatever reason, it’s really hard to keep that excitement and energy going when you’re two complete strangers. You don’t want to text too much (gotta save the good stuff for in person) but also if you let it fizzle it might be hard to get it back. That’s why I think it’s SO important to get Date 1 on the books ASAP — if you can, obviously!m (Agree with you though; if she’s on vacation best not to keep texting)

    Liked by 1 person

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