First Date Advice for Best Friends?

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Does anyone have any advice? My best friend and I are going on a date over the weekend of Halloween and I’m not sure how to best look at the night, not even sure the best place/things to do since she’s my best friend. We both have these feelings for each other that have developed over the past half year. So the typical “questions” you might ask are kind of void since we already know a lot about each other.

Just any advice is welcomed, thank you.
 
Don’t be surprised if things wind up getting awkward between you two.

Source: Experience.
 
She’s one of your best friends; you can play it by ear. You don’t need a plan.

You might, however, start with this: “Sarah, you’re one of my best friends. In my mind, there is nothing better than to fall in love with and marry your best friend. Those are the lucky couples. One of the worst things, though, can be falling in love with your best friend, but your best friend doesn’t fall in love with you back. Can we agree right now that if we decide we want to go back to being friends without romance, we’ll be honest about it, say so, and accept it? Because of course there is the third possibility, which is that neither of us feel romance for the other but neither wants to hurt the other by saying so and so no one says anything. That would be silly and pathetic at the same time.”

“No one is more important to me than you are, but this might not work out. It certainly may not work out in anything like a hurry. We’re going to have to wait and see. I promise you, though, that if you decide a romance is not in the cards, I will be a good sport about it. I promise you that I will respect your time line, and if you want a commitment that I’m not ready for, I will not ask you to wait around for me. I hope we do hit it off, because whoever marries you will be one lucky man, but I want to look out for you and the friendship we already have, so I’m saying that up front. If you want to make me happy, find the man who will make you happy, even if that isn’t me.”

That doesn’t guarantee that there will be no awkward stretches ahead of you–the rules of romance will not be re-written for you!–but even so she’ll thank you for that, I think. 🙂
 
Do everything the same. However, if you think she looks nice, tell her rather than keeping it to yourself. If you want to hold her hand, do it. If I was dating my friend and he turned into “date guy” all of a sudden it would scare me off. Be yourself, be the same person you’ve always been to her, just don’t hold back with any romances you might feel.
 
Dates, as such, are confrontative and self conscious. But doing something together wuth a friend, something both like, is normal, natural, and MUCH more conducive to a healthy and informed relationship – to friendship. Which is basic to a successful future, whether with that partnrr or someone else.

Respect is the cornerstone of true love, and its root is in friendship, not in forced intimacy, which is what much ‘dating’ often is.

The secret is to share some time in an activity you both enjoy.

Let it play out by itself. Don’t force or anticipate some preconception …
 
AaronSawyer said:
Does anyone have any advice? My best friend and I are going on a date over the weekend of Halloween and I’m not sure how to best look at the night, not even sure the best place/things to do since she’s my best friend. We both have these feelings for each other that have developed over the past half year. So the typical “questions” you might ask are kind of void since we already know a lot about each other.

Just any advice is welcomed, thank you.
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It’s important for you to be able to slice through any awkward moments and carry on a conversation. If that is a problem in a short time, I would suggest a movie so that you two are together but not necessarily talking.

Use your knowledge of each other to your advantage in creating conversation. I think you can probably discuss family or Catholic faith or more advanced topics like current events that people who don’t know each may be avoiding to start off with. Also, ask her open-ended questions and put the spotlight on her.

As a guy, you need to take the lead on this.

However you do it, you’ve got to have a bounce in your step and you must flirt with her in conversation if you want to keep it more than a friendship.

If it gets awkward a lot, she will not be attracted to you romantically.
 
FrenzyJen said:
Do everything the same. However, if you think she looks nice, tell her rather than keeping it to yourself. If you want to hold her hand, do it. If I was dating my friend and he turned into “date guy” all of a sudden it would scare me off. Be yourself, be the same person you’ve always been to her, just don’t hold back with any romances you might feel.
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Probably not a good idea for him to tell her he likes her right off the bat, even if it’s true, unless he’s absolutely sure she feels the same, and I don’t get that vibe from his post. This sounds like two friends who are going to try out dating, more or less.

You mention getting scared away, and I think we both know such a proclamation of “i like you” could do it.

In these situations the guy needs to flirt, be funny but not overly dramatic as though the fate of the world depended on this.
 
SuperLuigi said:
Probably not a good idea for him to tell her he likes her right off the bat, even if it’s true, unless he’s absolutely sure she feels the same, and I don’t get that vibe from his post. This sounds like two friends who are going to try out dating, more or less.

You mention getting scared away, and I think we both know such a proclamation of “i like you” could do it.

In these situations the guy needs to flirt, be funny but not overly dramatic as though the fate of the world depended on this.
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Yes, I’d stick with the “if this happens, let’s handle it this way”, not “I’m head over heels with you, so what do you say?” You can tell someone that they’re attractive without implying that you’ve fallen in the deep end already, and it could be a relief to hear “if one of us falls and the other doesn’t, oh well. At least we’ll still be friends…”
 
SuperLuigi said:
Probably not a good idea for him to tell her he likes her right off the bat, even if it’s true, unless he’s absolutely sure she feels the same, and I don’t get that vibe from his post. This sounds like two friends who are going to try out dating, more or less.

You mention getting scared away, and I think we both know such a proclamation of “i like you” could do it.

In these situations the guy needs to flirt, be funny but not overly dramatic as though the fate of the world depended on this.
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Oh no, I didn’t mean get down on his knees and proclaim his undying love on their first date. That’s exactly what I mean about getting scared away. I meant more that if they have only been friends up to this point, perhaps he could inch the other direction, i.e., a compliment about her hair or outfit that might be odd for a friendship, but it would have it’s place in a date/dating relationship.
 
Keep it simple. Go somewhere fun and light. We went to a swing dance club meeting on campus. My husband and I started out as friends so it can definitely work.
 
Contrary to much advice already given, I do not think awkwardness is a great problem to be avoided at all costs. The greater problem is finding a way to transition from friends to dating. Awkwardness almost always accompanies the early stages of dating and so may in fact help.

Also, I think it is important to plan activities that are in keeping with the change. Don’t keep doing what you’ve been doing as friends. Plan activities that people do when they date. You want to be able to see each other in this new light, in this new context.

And do all the things that you would ordinarily do on a date. Bring her flowers. Compliment her on the way she looks. This in particular will signal that you see her differently.
 
underacloud said:
Contrary to much advice already given, I do not think awkwardness is a great problem to be avoided at all costs. The greater problem is finding a way to transition from friends to dating. Awkwardness almost always accompanies the early stages of dating and so may in fact help.

Also, I think it is important to plan activities that are in keeping with the change. Don’t keep doing what you’ve been doing as friends. Plan activities that people do when they date. You want to be able to see each other in this new light, in this new context.

And do all the things that you would ordinarily do on a date. Bring her flowers. Compliment her on the way she looks. This in particular will signal that you see her differently.
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This is good advice, too. The advantage of dating a friend is that you can bring the flowers and dress up or whatever it is you usually do, and then say, “This is what I normally do for dates…do you like it? It’s a relief to have a date I can actually ask an honest question!”

(My husband let me know, for instance, that perfume is not appreciated. He had the bluntness of a friend. We still laugh about that!)
 
My fiancee and I started as good friends and after a.couple of years we transitioned to.dating. my best advice, play it by ear and just be yourself.and 've sincere and direct about how you feel. To us when we went out in an official.first date with the purpose of transitioning, it wasn’t awkward at all, not one bit so I cannot see why others are talking about awkwardness. You may be a little nervous before but sincerely, to me there was zero awkwardness. If you are going on a date with someone who you’ve been friends for a while, you are already comfortable with that person and is quite obvious what the intention is, so at least both of us had that pretty clear on our head. My fiance showed up with flowers for our first date, we went to a restaurant and started holding hands at the restaurant and after that we started talking about how we felt for each other. The only difference between that first date and other previous times we had been out as friends was that we were holding hands and that we officially agreed it was the beginning of our relationship, everything else was the same.
 
SuperLuigi said:
Probably not a good idea for him to tell her he likes her right off the bat, even if it’s true, unless he’s absolutely sure she feels the same, and I don’t get that vibe from his post. This sounds like two friends who are going to try out dating, more or less.

You mention getting scared away, and I think we both know such a proclamation of “i like you” could do it.

In these situations the guy needs to flirt, be funny but not overly dramatic as though the fate of the world depended on this.
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If two people who have been friends for a while are going in an official date, it is not precisely because they want to remain friends. If she accepted going with him on.a date is obvious she is expecting this as the step to the next level. The flirting is for people who just met and are going into a date after just recently met. I don’t think he has to tell her I like you the minute she opens the door but he needs to do way more than flirting. Probably holding her hand, putting his arm around her shoulders, tell her she looks pretty, how special she is and after.some time then just talk about their feelings.
 
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