Ask Abby, Lifestyle

Ask Abby (or Analise): A beginner’s guide to first dates if you want a second one

Dear Abby: I really like someone and I want to make my move. The thing is, I don’t know how to approach a first date. Please help me figure out what to do to impress them enough to score the second date!

Annika Morris | Senior Graphic Artist

First dates can be both scary and tricky to navigate. You’ve taken a leap of faith by just asking the person out, but now you really have to commit to spending one-on-one time with them for at least an hour.

There’s also a lot of uncertainty. Where should you go? Should you pick them up? What questions should you be asking?

So, if you’re trying to solicit some advice from a dating expert, I’d be happy to share some of my personal guidelines on how to take someone out.

Before the date

I think the time that two people share prior to the date is as equally as important as the main event itself, and trust me, there is an etiquette that you should follow. 

First and foremost, communication is key. Be careful that you’re not going overkill, especially if you haven’t met the person beforehand. If you text too much, then there’s less to talk about on the actual date.

I would recommend discussing the parameters of what the date will involve in advance and following up the day of. Leaving people hanging is immature —-so if you want to show someone that you respect their time, make sure to confirm.

Here’s an insider tip: if you really want to prove that you’re invested in the date, pick them up. Walk, bike, train or Uber — your pick. Not only does going to the actual date together help ease the nerves, but it also shows that you’re capable of following through on a plan from start to finish. Full effort gets full points. 

The date!

Believe me, where you go and what you do matters.

If you want a chance at a second date, do not do a movie on the first date —- unless the occasion is preceded or followed by a more intimate arrangement, such as dinner. 

It’s critical you test your chemistry on the first date, and this is your chance to dive a bit below surface level. Here are some bases you should touch upon: What are they truly like as a person? What are their morals? Do you have similar interests? 

In terms of atmosphere, I would also advise against a super informal or overly crowded event to help foster the intimacy of a first date.

Coffee shops can be crowded, noisy and limited when it comes to seating –– so it can be really hard to get to know the person who you’re seeing amid the commotion. 

Taking timing into account, I would stray from making the first date an early endeavor. 

This can be successful for some, but I think something in the late afternoon or evening always works better. It gives the date something crucial: more room for a clear start and stop time. 

Dinner at 7 p.m.? You’ll probably finish around 8:30 p.m. If the date is going well, continue it onward, but if things head south, it’s already pretty late and you should probably get going.

Most importantly, a first date should commence in a public setting. Not only does that make me feel more safe, but it also removes the nerves that come with being welcomed into someone’s personal space.

So if you’re asking Abby (or Analise), my acceptable first date activities include: 

  • Dinner and a movie
  • Mini golf
  • Pottery painting 
  • Museum/art gallery visit 
  • A concert 

But the premise of the date itself isn’t enough to warrant another one. What’s imperative is how you act.

Here’s some advice: Be yourself. Don’t bring up exes or make your date interview you. Instead, ask questions back and be personable. Hold the door open for your date, always be polite and, most importantly, don’t be shy with humor. Everyone loves someone who can make them laugh. After all, it takes the edge off.

Oh, and you probably want to know who should pay for the date. I’d say the person who does the asking out should, though the cost of some activities can be split. 


If you went on the date together, it’s only right that you bring your date back home. Unless they insist otherwise, I think it’s a classy way to fully round out the date.

Now, just because the first date went well does not mean you have things in the bag. If anything, it’s how you follow up after a first date that really dictates where things will go from there.

You can’t miss one of the most critical steps in dating: the follow-up text. Assuming things went well, it’s not only polite to follow up with a short and sweet message that thanks them for a wonderful evening, but it’s necessary to end the night with a final showcase of interest.

A simple, “I really enjoyed going out with you tonight, you’re awesome to talk to!” will do. If you’re feeling ambitious, maybe ask when they’re free again. 

In the event that your date doesn’t answer, don’t be pushy. Maybe things didn’t go as well as you thought, but there’s no use in getting hung up on someone who isn’t reciprocating. 

Should we kiss?

I’m sure what you’re all dying to know is this: Should you share a kiss on the first date? 

Whether it’s a peck, smooch or a full-on makeout, I’m going to have to say no. 

It’s not that there’s any shame in that game, but I’m just not sure if you can fully gauge a person’s boundaries in that short of a time frame.

Maybe this is a me thing, but I just think that holding off keeps things more passionate and interesting. In the end, who doesn’t like a little mystery? 

If you don’t, here’s a sure thing that I can guarantee once you reach the end of this edition: you got this.

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