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First Date With a Best Friend... How to Make it Matter...

Updated on September 21, 2009

Transitioning from Friendzone to Lover

You and your "bon chum" have had "the talk..." and have had the courage to admit that there is more between the two of you than the friendship that you have cultivate over the years. Good for you! That leap... was a tremendous one... and now you have to look forward to the dreaded "first date" with the one person that knows you like no other.

Some would say that the "first date" with a friend you wish to transition from platonic into a relationship is one that is more stressful than that with a casual acquaintance or stranger. You have everything to lose and/or everything to gain.

That being said here are some tips to make that transition from friendship to relationship a memorable one... and one that will protect your interests no matter how the cookie crumbles.

Step 1: The Grand Gesture - The grand gesture or sentimental token you offer initially will set the pace and groundwork for the date and will make the bestowed nature of your true feelings more palitable upon their recipient. Even though the gesture is grand make sure it is a SMALL one. Nothing extravagant... only something memorable. The goal here is to let the friend know they matter to you without going overboard. For example, you can read their favourite book... remind that special friend that you remember the little things they have told you over the years about themselves. Or buy something small at the dollar store that reminds them of a special moment you two shared. Even sending them a post-card from an excursion you are on will undoubtedly let them know you are in their thoughts.

The idea here is to let that special friend know that you think of them and that they matter.

Step 2: The Invite - Suck it up princess. Now its's time to let them know that you feel more than friendship without overwhelming them with those feelings that you have bottled for a very long time. More often than not... this will take time for the other friend hearing this to come to terms with it. They may require space as you delicately spring on them that you wish to take the friendship to a different place.

Less is more here.

Step 3: Be Deliberate - So ask them out on a date. Be deliberate with your intentions! Let your friend know that this is MORE than a casual hangout at the local pub. This is something you have been planning and would like to enjoy their company on a different level. There is nothing worse than having different expectations about the date. You are hoping for romance and she bring along her friends! You see where I'm going.

When I say deliberate. Be deliberate. Say... "this means I am taking you out on Thursday." Wait for their response. And gauge their enthusiasm by their predisposition to your intentions.

Step 3: Relax - Congrats! They have accepted. So relax. That means at the outset they are at least curious and above-all interested in pursuing a leap with you! So keeping your cool and a clear head is clutch here. Don't get all puppy-dog and doe-eyed here. Confidence in your decision will set the tone to an enjoyable date. If you come on too strong you may push that chance into never-was land. So be careful here.

Step 4: Take the Entire Day - Take the entire day. This step is an important one. Your friend and you need some serious time to hammer out what it is that you are looking for and really try to drill-into the real nuts-and-bolts of what you want out of your platonic (or non-platonic) status. A quick coffee at the local Bucks just isn't going to cut it here.

Things are going to be awkward at first. So taking the entire day will allow time for the two of you to relax and to reconnect on a different level without the clock ticking to quickly. If they aren't willing to book an entire day with you... then you know right away that there intentions aren't the same as yours as far as "feelings" go.

Also, let your date know that you had other plans that day. That you took the time to re-arrange your schedule. That the date with a friend is a priority for you and that you really want to give it a try. Also, it lets the friend know that contrary to popular belief that...yes you have a life :)

Step 5: Don't Go Overboard - Start the date on a casual tone. Build the day like a crescendo... a climax. Nothing to overboard romantic right outa the gate. This is a must. Start out with a movie or a baseball game. Give the two of you time to start out in the comfort zone and to build on that throughout the day. As the invitor it is up to you to set the tone here and to build up the date as such. After the ball-game or movie move to a second venue...dinner at a quiet place or even better yet ... go back to your house and have an intimate candlight dinner for two there. At this point there will be no question that your intentions are romantic.

Don't go overboard. I repeat don't go overboard. Like having too much sap in a tree... so too can a much too formal first date overwhelm your other friend. Grow into the journey that the two of you are taking. As hard as I know it is not to want to fly them to Tuscany and go to an Opera... hold off... until that special point when your relationship has grown into something really intimate.

Step 6: Communicate - If you are nervous. Tell him/her. Communicate! There is nothing wrong with letting them know this! It shows that you are open and honest.  At the very least they will be relieved as chances are they are on the same wavelength... or knew already :)

Step 7: Up-close and Personal - Throughout the date close those physical boundaries by undertaking small but subtle entries into your friend's personal space. For example, brush their hand, touch feet, rub their shoulder or arm. Gauge their response. Do they turn red and giggle when you touch? Do they withdraw or do they reciprocate the tone of the phyiscal intimacy?

Again, don't go overboard. This is the most akward point of the date. This is the testing ground for your physical chemistry and to initiate "the kiss."

Step 8: The Kiss- Alright gentleman this is where we separate the men from the boys. I would recommend that the kiss be in the middle of the date when the two of you share "the moment" and he/she give you that "look." The boys know what I'm talking about here. The kiss is the most important signal on whether you have real physical chemistry to lift your friendship into more. So be forewarned that the expectations are higher on this kiss than probably any other date you two of had with others.

Gentle..and respectful here guys. Don't rip her face off with tongue. I know... again... years of pent up affection may try to come rushing out. But for the sake of a future with the two of you... try to refrain.

Step 9: Get the Hell Outa There - Desire is what it is. If she wants more than 2nd base. Guys get the hell outa dodge. I repeat... get the hell outa dodge. Why? Simple. You want to respect this one. She is your friend. She knows about all your devilish ways and if you truly do care about her... then you have to let her know that she is on a pedestal and that you respect her more. You want to learn to grow and learn about her. Well that is what you tell her anyway when you exit stage left.

What are the other reasons? Too much too soon will sabotage and lead to regret. This is a friend not a stranger or someone from the gym. It translates into respect and understanding... bottom line. If you are making out... you know you like each other. So what's the rush? There will be plenty of time for the other. Desire comes from yearning... cappish?

Step 10: The Follow-up - Alright so you have survived an entire day and a few kisses hopefully. The follow-up to the date is crucial. Be polite and send her a text or a call the next morning to say... hey... I had a great time (if you did of course). Leave the door open for another date. Simple and short. If you talk on the phone... don't make it longer than 5 minutes. Again, let her know enough to make her interested... anything longer than 5 minutes may put you right back in the friendzone.

Now, if things weren't as fun or enjoyable as you had built them up in your head to be. Hey, at least you tried. Let your friend know that no matter what happened that you two will always be friends and invite her out again... but this time at a more casual outing with others. This will pave things back into the friendzone with a little more ease and less akwardness.

Good luck! Above all kudos to you for having the courage to leap. It is all about the journey... not the destination. So focus on that. The years that the two of you have known each other have paved your road to get to this phase... and undoubtedly that truth and honesty will transcend your future as well.



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    • Lymond profile image

      Lymond 5 years ago from UK

      Ah! something with specifics and content at last, hopefully I can get past step 3 :-)

    • SweetiePie profile image

      SweetiePie 8 years ago from Southern California, USA

      Great advice and I am sure your hub can help many people. Hope you signed up for adsense so you can start earning on your writings here.