Should I Date My Best Friend? It's Not Always A Good Idea

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If you notice that you start having feelings for a friend — especially a close friend — it can feel totally overwhelming at first. You may start wondering if you're mistaking intimacy for romance, worrying that you're reading the signals completely wrong, and, of course, contemplating whether it's actually worth it to give it a shot. If you start to date a friend, even your best friend who you think you know so well, it can mean losing a friendship or, at the very least, damaging it. So how do you know if you should actually date your best friend?

Well, you need to ask yourself a few tough questions — and be honest with yourself. "Being honest about your feelings is necessary in all relationships, but in this instance, truth telling is paramount, or you can find yourselves giving each other a lot of mixed messages that could ruin your friendship and your chances for a real relationship in the future," relationship coach and psychic medium Cindi Sansone-Braff, author of Why Good People Can't Leave Bad Relationships, tells Bustle. Now, you can't predict how things will turn out if you do go for it. You can never be sure you're making the right decision until you try, but you can make sure that you've really thought it through before making any rash decisions, to give you the best shot at succeeding. Here's what experts say you should keep in mind.

1. Do You Think They're Into You?

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Firstly, before you go for anything with your best friend, you want to be as sure as you can be that there could be feelings there — on both sides. And when someone likes you, there's usually a few telltale signs. For some, it's all in the eyes. "This can be a fine line, but often you can tell in the way that they look at you," Danielle Sepulveres, sex educator and author of Losing It: The Semi-Scandalous Story of an Ex-Virgin, tells Bustle. "Strong eye contact that results in a vibe that feels almost palpable, even if you're not reciprocating." Make sure that you can detect something reciprocal — whether it's eye contact or flirting — before you move forward.

2. Can You Imagine The Dynamic Shift?

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You might be attracted to this person and you might even feel a spark, but be honest — can you really imagine the transition into dating them? Can you picture yourself with them in a romantic setting? "I think that if you are more comfortable just hanging out with a person than when you are on a date, the friendship card might be too strong to ignore," Rob Alex, who created Sexy Challenges and Mission Date Night with his wife, tells Bustle. "If you feel different when you are on an official date with this person, it is time to step back and figure out if your friendship with them is more valuable than a possible romantic relationship." If even thinking about being on a date with them makes you uncomfortable rather than just feeling scary and new, you need to pay attention to this. I have had plenty of friends with benefits set-ups that have been great, but the idea of me on an actual date with any of them was cringeworthy.

3. Do Your Values Line Up?

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A good relationship involves way more than just two friends who are attracted to one another, so this is the most important thing to ask yourself: Do your values line up? "The best way to tell if you are better off as friends is [asking yourself] how much you respect their values," life coach Kali Rogers tells Bustle. "We can be friends with a lot of people with varying values, but it's totally different when you start dating them... If you love being around someone but don't necessarily see eye to eye on things that are pretty important to you, it's best to stay friends."

I have lots of close friends who I love dearly and who I love to debate with — in fact, disagreeing is often totally fine, even when you're best friends. But I wouldn't want to be in a relationship with someone who was so opposite to me or doesn't share my core values. So look at this best friend of yours and decide if you actually have the compatibility for a relationship or just an amazing friendship. And if you don't feel confident, you may not want to ruin a great thing.

Best friendships can be incredibly intimate, rewarding, and special, but just because you're best friends with someone doesn't mean you should date them. Hell, just because you're best friends and attracted to someone doesn't mean you should either. Be honest about how you both feel, about what dating them would look like, and about how compatible your values really are. Then, it's up to you whether taking the leap is worth a shot.