Plan a new, exciting activity.
Think about what she might enjoy doing. If you’ve already been out to dinner or to see a movie together, try doing something different. It will be a nice change from the relationship you two have had so far, and it can be a fun way to get to know each other more. You could go out for drinks, get some coffee, try roller skating, go mini golfing, or take a walk in nature. Anything you two haven’t done together already is fair game! Since you already know her, you can think about what she’s told you about her favorite things to do. If she’s outdoorsy, a hike might be fun. If she loves board games, consider having a game night.
Dress to impress.
Show her that you’re taking this date seriously. You don’t have to go out and rent a tux or a ball gown (especially if you’re just going out for coffee), but put a little effort into your appearance. The better you look, the better you’ll feel, too. It’s a good idea to dress for the occasion. A business casual slacks and button-down look might be great for dinner, but jeans and a nice T-shirt is fine for going out to a ball game.
Talk about stuff you’d normally talk about.
There’s no need to prepare conversation topics ahead of time. If you two know each other already, then just chat about what you used to chat about. See how she’s doing, how work or school is going, and what her hobbies are like. Even though you’re on a date, you don’t have to pretend you don’t know her at all. For instance, you might say, “So, how’s your brother doing?” or, “How’s the new apartment treating you?” There is one exception: if you know her through work, try to avoid talking about your jobs the entire time. It’s not super romantic, and it can solidify the relationship you two already have instead of moving it forward.
Ask her questions about herself.
If you already know some stuff, dive a little deeper. See what her family is like, who her oldest friend is, or why she moved to your city in the first place. You may already know her basic info, so it’s time to get to know her a little more. Try questions like: “Who are you closest to in your family?” “What made you pick your major in college?” “What’s your favorite thing about living here?”
Use your relationship to inspire witty banter.
Call back to inside jokes or funny things that have happened in the past. Don’t be afraid to bring up silly stuff that you two have already talked about. If you two are already close, you shouldn’t have a problem just chatting and being silly with each other. For instance, you might talk about a funny thing that happened to the both of you: “Remember the time that seagull stole your ice cream cone? It just took it right out of your hands!” Or, if she’s a coworker of yours, you might say, “Remember what Jerry said at the meeting this morning? I was trying so hard not to laugh out loud.”
Flirt with her.
Test the waters by giving her a compliment or touching her shoulder. Remember that the aim here is to move your relationship forward, not just stay friends or acquaintances. Touch her on the arm, tell her she looks nice, and keep making eye contact with her. You could say something like, “Wow, that dress looks stunning on you” or, “You have an amazing laugh.” If she doesn't reciprocate, it’s not necessarily a bad sign—she might just be nervous.
Tell her why you like her.
Be clear about your intentions and that you like her a lot. Let her know why you asked her out and what you’ve enjoyed about your relationship so far. It will let her know that you’re serious about becoming more than friends. Try something like, “I’m really glad we’re going out tonight, just the two of us. I always have so much fun hanging with you in a group, and I can’t wait to get to know you one on one.” Or, if you’re on a date with your ex, you could say, “I’m really glad we’re trying this again. I think we’ve both grown a lot, and I’m excited about our future together.”
Embrace any awkwardness.
It’s okay if it takes a few tries to work out all the kinks. If you two catch a case of the giggles or have an awkward pause in your conversation, that’s alright! Push through it and continue on your date. Awkwardness is something you both can work on, so don’t let it put you off.
Take things slow.
There’s no need to rush into an intimate relationship. Even if you’ve known this person for a while, treat her like you’d treat anyone else. If it feels right, you two can share a kiss on the first date, but there’s no pressure to go any further if you don’t want to. Taking things slow with her will also show her that you’re serious about your relationship.
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