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About To Date A Friend? This Is What You Should Know.
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About To Date A Friend? This Is What You Should Know.

Thinking about taking things to another level? Pause and read this first.

Love & Relationships

OK. I'm gonna start this off by saying, out the gate, that dating a friend is a bit of a complex topic. On one hand, I'm a huge advocate of it because I wholeheartedly agree with what the late and great R&B singer Johnny Kemp once said when he sang, "the best of friends can be lovers, after all". Indeed. In fact, let me tell it, a lot of marriages would go the distance if folks actually married, not just "a friend" but someone they consider to be their best (highest quality, highest standing, most excellent, most suitable) friend. Why? Basically, because we tend to have so much more tolerance, understanding and willingness to work things out when someone is our very best friend. When we see them as anything less, not so much.


There is a flip to this, though. As someone who was once in a relationship with one of my best friends for several years and is no longer friends with that person now, there are a few things that you should think about long and hard before making that kind of shift in your relational dynamic. For me, I regret getting involved with this particular close friend for all kinds of reasons. Again, not because I don't rally for friends transitioning into more-than-friends. It was because he was into me, I wasn't all that into him and yet I convinced myself that, since he was such a good guy, I should talk myself into making "it" happen anyway. For the skimmers out here, let me just say that if you've got to convince yourself to be with anyone (or it looks like they are trying to "talk themselves into" being with you), that is absolutely NOT a good reason to make a relationship happen. You deserve to be with someone who you're totally into, "they" deserve to know what that feels like — and vice versa.

Still, if you and your friend have a mutual attraction, you do feel a bit of a mutual spark, you're both currently single and there is a part of you that wonders if you both should take things to the next level, here are some things that I highly recommend that you strongly consider — so that making that move can significantly up your chances of proving itself to be totally worth the risk.

Know That Yes, a Relationship WILL Change Things

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When it comes from going from friends to more-than-friends, where some people mess up is they actually tell themselves that not much will change after the switch is made. In their minds, all that will really happen is they'll go out more and maybe become sexually involved. First of all, becoming sexually involved with someone changes things (it's designed to); if not immediately, eventually. Secondly, the mere fact that the two of you decided to become "more", that speaks to an immediate shift and you wanting one. And sometimes — no, most times — there's no going back once you do.

Can you see the future? Oh, the power we would have if we could. We can't and so yes, making this move is a bit of a gamble. All I'm saying is this is definitely not something that should "just happen". You need to be realistic about the fact that going from friends to more-than-friends can have a ton of benefits. It could also bring about some regret if you're not careful as well.

Whatever You Expect to Switch Up, Discuss It. Beforehand.

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There's someone I know who was friends with someone else, dated them to the point of being engaged, broke up with their fiancée, remained friends (see, it happens) and now, all of these years later, he and his ex are considering making a go of it again. What's the hesitancy? Well, back in the day, the goal was marriage. He's divorced now and has no real interest in getting married again while his ex has never been married before. While she's not sure if jumping the broom is a true desire of hers, he cares enough about her and what they currently share that he wants to make sure that he doesn't end up wasting her time or standing in the way of the kind of relationship that could lead to marriage for her, with someone else, in the future.

That's some grown-up ish right there. Problem is, he's been discussing all of this with me more than with her because he wonders if expressing all of this could make things super awkward and possibly ruin the potential of something romantic. Maybe. Yet what's worse is to go ahead and start dating and/or having sex, with both of them assuming one thing, when they both couldn't be further off the mark.

If there is a benefit that comes with dating a friend, it should be that the two of you already are pretty good at communicating, so why feel uncomfortable with sharing your heart about being in a relationship or even what your fears are concerning it? The best that can happen is you both discover you're on the same page. The worst is realizing that you're not and so you continue on as friends. Right?

Don’t Do It As a Form of Settling

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Sometimes, people consider dating a friend out of pure loneliness — shoot, even sheer desperation. Since there are no current prospects in their space, they tell themselves that since they've been spending so much time with their friend in the first place, why not test things out to see if becoming more serious is a good idea.

The guy that I was talking about in the intro? That is a part of what I had going on. I wasn't desperate. I had semi-recently broken up with someone else and so I was a little lonely, though. However, the biggest point was I told myself, "I mean, we hang out all of the time and I tell him everything anyway. All I've got to do is have sex with him. It can't be that big of a shift." Oh, yes it was. Suddenly, the guys I used to tell him about and get advice on, he didn't want me talking to and the hangouts that used to happen so effortlessly, we both wanted more from (he wanted them to happen more often and I wanted him to be much more romantic when they did).

Looking back, because we had been such good friends and that served as the foundation of our relationship, that's what made everything last for as long as I did. Yet I would be lying if I didn't say that I settled — big time. I didn't love him as more than a friend. I was in love with the idea of loving him as more than a friend. And, because of that, I tolerated more than I ever should have. He sucked at birthdays and special occasions. Financially, I was in a more stable place (read between the lines on that one). When he had sex with someone else, I stayed because I processed it as "holding down my friend" when I should've taken it as my "get out jail free" card. Literally.

The takeaway here is, when you know that you're settling, in anything, it usually starts to bring on feelings of resentment — and that can never (ever) be good. So, if you're considering dating a friend because "you've got nothing better to do" — don't. Take it from someone who did it that way and lost time that I will never get back.

What Are the Benefits of Going to the Next Level?

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I mean, if you're going to think about this from all perspectives, I had to share with you some of the downside potential. Now let's hit on some of the immense perks. Dating a friend means you're getting involved with someone you already know (I mean, really know). Dating a friend means you're taking things up a notch with someone you trust. Dating a friend means that you can move past that "dating the representative" BS that leaves a lot of people totally disillusioned; while there is another side to one another that you will encounter, because you started out as friends, you tend to already know a lot of their flaws, triggers, history and issues (as they do you). And since you both decided to move forward anyway, it's all good.

If they are a close friend, chances are, your family members and other close friends already know them (or know a lot about them) and have accepted them as a part of your world. Dating a friend also means that you can be certain that you both have each other's best interest at heart — that you're not just "playin' each other". All of these are huge wins. They really are.

Remember to Keep the Friendship Your Top Priority

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I'm thinking that we all can pretty much agree that the foundation of any relationship should be a friendship. That's why, although there are certainly exceptions to the rule, overall, I'm a bit leery of folks going from 0-100 in only a few months.

I mean, if it took you a couple of years to really trust your girlfriends, why would you marry a guy you've only been seeing (including just met him) for a half a year? While it's kind of a rhetorical question, the answer I've got is a lot of folks are so busy trying to be "in love" that they underestimate how important it is to be "in like" and if you ask any married couple which will get you through the hard times, I can guarantee that at least 90 percent will say that it's the latter.

That's why, if you and your friend do indeed decide to date each other, there's got to be a mutual commitment to keep your friendship as the top priority. What I mean that by that is you need to remain real with one another (even if something is hard to hear), that you both are practical about where things stand (even if it's tempting for one of you to romanticize things to where you are being a bit unrealistic about your expectations) and that you nurture the friendship over feeding the relationship. What I mean by that is you both check in to make sure that you feel like the friendship is still intact.

Because, take it from me, sometimes, when you're dating a friend, you can be so focused on what you think a relationship should be like that you don't even ask yourself if your friendship (and friend) is good — if all of the things that caused you to become friends in the first place are still in a healthy space.

Be Honest: Are You Willing to Risk Ultimately Losing the Friendship?

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I was recently talking to someone about how heartbroken they currently are because they dated a friend, it didn't work out and what they are now grieving is the end of the relationship and the friendship. Why did it have to cost them both? Because the reality is, even when you are super close with someone on a friendship level, there are some things that you can only experience in a relationship and if things like disloyalty, wanting different things from the relationship, being emotionally hurt on a relational level happens, sometimes that can taint the friendship because you just don't see your friend in the same way.

Personally, if I had really thought about if I was willing to lose my friendship for a chance at a relationship, with all that I now know, the answer wouldn't just be "no". It would be "hell no" because, although he and I are now peaceful, there's just too much water under the bridge at this point.

Again, I hope you don't close out this article and be like, "Damn. Dating a friend sucks" because it really doesn't have to. It's just important that you and your friend are open, honest and really clear about why you're doing it and what you ultimately hope to gain from it. If that happens, again, your odds of success are really good. On the flip, if you're not sure, keep what you already know is great — the friendship.

Because if it's meant to be, you both will know at the right time, there will be a mutual level of peace and the relationship will also move forward into something else — a long-term commitment. If you or he just doesn't feel right about all of that, at least for now, leave well enough alone, chile. Please. Thank me later.

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