6 Crucial Things You Should Consider Before Dating A Friend
Embarking on a romantic journey with a friend might turn out to be the most wonderful experience of your life, no doubt about it.
However, before reaching that thrilling point, there are several hurdles to clear in order to navigate the unique emotional landscape you now find yourself in.
My boyfriend and I began as close friends, and trust me… it was quite the challenge before I learned how to conduct myself, now that our relationship was evolving beyond mere friendship and my feelings had intensified significantly.
The moment he kissed me for the first time was incredibly awkward, but not due to any lack of skill (believe me, he knows how to kiss), rather because we were both filled with uncertainty and hesitance.
As we mustered the courage to go for it, the moment unfolded in a haze, resulting in something quite forgettable.
Fortunately, we shared an understanding that we had the potential for much more, which gave us the motivation to try again.
The initial days are undoubtedly amongst the strangest times.


It might depend on the level of intimacy you shared as friends, but for us, being quite close meant we were hesitant to jeopardize our friendship for a relationship that could potentially fail.
Mastering how to act when transitioning to a status greater than just two close pals can be intimidating.
Especially as certain feelings arise and the sense of attachment towards him starts to deepen.
It becomes overwhelming, as you sense that this is leading to something new and thrilling, yet the intense affection you’re experiencing is also frightening.
Because if things don’t pan out, you could end up losing one of your best pals.
For us, I count my blessings that we persevered, because it’s been just over a year, and I’ve honestly never experienced a healthier and more joyful relationship.
The bond we had as friends is what truly propelled us forward.
We were already at ease with each other, eliminating the need for those awkward discussions that might reveal something alarming and drive one of us away.



I already possessed all the knowledge about him, giving me the assurance and confidence needed to continue pursing this path.
When you sense that there’s more to your relationship than mere friendship, my genuine suggestion is to pursue it!
I wouldn’t be the person I am today if I hadn’t had the courage to transition from friendship to romance.
Without taking the chance, you may never discover what you stand to lose or gain, and if it blossoms, it will feel even more rewarding since he was your friend first.
There’s no definitive guide on transitioning from friends to partners, yet some elements will definitely influence the experience, and it’s wise to educate yourself before taking the plunge.
If you’re seriously thinking about starting a romantic relationship with a friend, here are a few things to keep in mind before diving in!
Consider initiating some playful flirting to gauge the situation



It can be tough to interpret his feelings, especially since you both share a strong connection and you know he values your friendship immensely.
That’s the crux of the matter. He has a lot of affection for you as a friend, yet you’re hoping it evolves into something deeper!
How can you tell if there might be something beyond platonic feelings in a fun, playful friendship?
This is how I figured it out. Whenever I went shopping, I would snap a cute selfie in a new outfit and send it to him, seeking his advice on whether to purchase it or not.
Make sure your outfit is flirty and eye-catching, so he understands your intent. His reaction will give you insight into your relationship’s status.
His responses were often playful and flirty, not typical friend banter, which confirmed my suspicion that he was flirting back!
This encouraged me to seriously consider dating him.
I recommend testing the waters first to ensure there’s a genuine connection before taking a leap into a more serious relationship.
Ensure a strong friendship foundation before proceeding



If you’re contemplating a romantic relationship with a friend, ensure that this person is a true, dependable friend instead of someone who might bail on you when things get rocky.
Your friend’s behavior is likely a reflection of what he would be like as a partner.
Can he be counted on in tough moments? Is he truly someone you can trust completely? Would he come to your aid at 3am if you were in distress?
All of these factors need serious consideration before you delve into a deeper connection.
Given your closeness, you probably know him well. If you have a deep, meaningful friendship characterized by genuine care and respect, then you’re clear to pursue this relationship!
However, if you observe his interactions with other women and it bothers you, reflect on how he may treat you similarly.
Is that treatment something you’d be okay with?
Deep inside, you know his true nature. Don’t convince yourself he’d act differently with you. What you see is generally what you get.
Ensure that he is a trustworthy and sincere part of your life before making any significant commitments.
Evaluate your true intentions behind wanting to date him



Be truthful with yourself, and do not allow your current feelings of loneliness or diminished faith in love to lead you astray.
You don’t want to enter a relationship with a friend out of desperation for companionship.
Engaging in a relationship with anyone due to loneliness would create chaos, as everyone would be rushing into relationships recklessly.
It’s vital to ensure you have the right motivations for considering this path.
Above all, you must have genuine feelings that go beyond simple friendship.
There’s no sense in pursuing something that’s merely friendly without deeper emotions involved.
Once you’re confident that your feelings have progressed past mere friendship, you’re ready to move forward.
It’s essential that you share common interests as well. Starting something without mutual footing regarding future goals is risky.
Though he provides comfort and security, those traits alone are not sufficient to initiate a romantic relationship!
A physical attraction is crucial as well, and you must genuinely wish to be closer to him romantically.
If that’s not the case, it likely won’t end well, and you’ll find yourself back at square one.
If you’re genuinely committed to this idea, shift from friendship to romance
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Initially, it’s completely natural to fret about what this might do to your friendship should it not pan out.
You’re concerned about losing a fantastic friend, and it’s understandable.
However, at some point, you’ll need to shift gears and stop viewing him just as a friend, focusing instead on making it work as a couple.
As long as you remain fixated on the future and its potential impacts, you won’t be able to wholeheartedly engage in this.
You are entitled to happiness. You owe it to yourself to give this connection a genuine chance.
The key to succeeding is to invest significant effort and ensure you’re both aligned towards creating a beautiful goal – a fulfilled and loving relationship.
Utilize your friendship as the solid base upon which to construct a deeper connection that fosters intimacy exclusive to couples.
Let go of all the potential pitfalls, and concentrate on the beautiful thing you’re trying to cultivate together.
Every new relationship carries the risk of fizzling out, but that shouldn’t lead you to doubt yourself and sabotage something that may turn out to be the best experience of your life.
Maintain your developing romance discreet and refrain from sharing too much with friends in common



It’s likely that both of you share some friends, and they may inevitably find out about your relationship.
This is perfectly normal; curiosity about two friends suddenly dating is expected.
However, the key is to keep your mutual friends at a slight distance.
Relationships are tough enough without the added pressure of people wanting to know every little detail of your budding romance.
You can share simple updates.
Casually mention that things are going well and that you’re both satisfied with how it’s progressing, but avoid revealing too much information. Keep the deeper details to yourselves.
The spotlight can quickly become overwhelming, and you really don’t need additional pressure or incessant questions when you might not even have all the answers.
Until you gain clarity and truly understand where things stand and what your intentions are, it’s best to maintain privacy; it ultimately benefits the relationship.
Only once you’ve solidified things and clearly understand your path together, can you openly talk to friends about it.
This way, it won’t harass or pressure you into unforeseen complications.
Moreover, aren’t secret romances just thrilling?
Having this extraordinary, passionate new experience all to yourselves, hidden from the world?
I know that was my favorite aspect personally.
He was my secret crush for as long as we could keep it that way!
Understand that the initial phase is likely to be quite awkward (and that’s perfectly alright!)



Every amazing new adventure often starts with a bit of awkwardness, and you will not be different.
Your initial sexual experience will likely not live up to the passionate fantasy you’ve envisioned.
It might well be dreamy, but odds are it won’t be quite as you imagine.
The expectations and the vision of what it ought to be will heavily influence the actual experience.
I’m not implying it will be unpleasant—just a tad uncomfortable, in an adorably endearing way, honestly.
Though you may feel very close, engaging in sex adds a layer of intimacy that is new for both of you, and you will need to explore each other’s bodies before reaching that fiery and passionate stage.
From my own encounters, the second experience significantly improves!
Your first attempt is essentially about getting familiar with each other on the most intimate level, figuring out what clicks between you.
You’ll experiment, discover what sensations are enjoyable, and know precisely what to try (or what to avoid) for next time.
The most important part is that if there is genuine chemistry, you’ll have the ability to laugh it off and move on.
You will find the situation endearing and funny, and when it’s over, you can chuckle together before sinking into peaceful rest in his embrace.
Believe me; it will feel just right. Just give it a few tries, and you’ll get the hang of things!