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See When Should You Try This? to learn more about when trying to turn a friendship into romance might be a good course of action.
Understanding Your Love Interest
Discover her conscious romantic standards. Some of these will be fairly obvious. She may want to be with someone with the same religious values, or a non-smoker. You don't have to necessarily meet all of her criteria, but you should avoid failing to meet her standards, as this will often remove you from her romantic pool. Make a list of features shared by all her previous boyfriends. These are likely things she makes it a priority to find in her romantic interests, and may be characteristics you should consider cultivating in yourself.
Figure out her unconscious criteria. This is often related to her own personal characteristics. Many people, including your female friend, search for a partner with the same positive characteristics that they like in themselves, but want qualities in a partner that are opposite to the things they dislike about themselves. After you find out some of the things she dislikes about herself, show her how you can compliment those areas with your strengths. You could say: I hate how competitive I am. I think I'd be much happier if I learned to enjoy things instead of making them into a competition. What about you? If you could change one thing about yourself, what would it be?"
Chart out her love map. Psychologists have discovered that as we go through life, we start developing a "love map," or an idea of who we want to be in a relationship. Some aspects of her love map will be conscious, like she might want an educated partner, but these can also be subconscious preferences, like how affectionate her partner is. By understanding her love map, you can meet her needs better. Though there are many variables that will affect her particular love map, look for these criteria to guide you in understanding her love map: The expectation of romantic relationships to involve commitment. The accepted duration for a relationship. A belief that the "right" romantic partner will bring satisfaction. The ideal length of time acceptable before arriving at a romantic commitment (saying “I love you”). The length of time between a breakup and becoming involved in a new relationship. The acceptable length of time spent waiting for a partner to commit. The level of acceptable disagreement on basic life values. Whether or not an argument with a partner is exciting or frightening. Whether or not a polyamorous relationship is acceptable. The amount of time expected to be spent separate from friends, family, and social events/obligations.
Meet her friends. Be on your best behavior when you do so, because these people will give you a window into her life that few others will have at their disposal. If you're serious about your love for your female friend, expressing your genuine caring for her to her friends will likely earn you their respect, and maybe their approval. You don't have to bare your heart and confess your love to her friends; try to earn the respect of her friends by being a nice guy. Explain how you've noticed she's been stressed and ask what they think you can do. Or mention that she's been a good friend and you want to do something nice, what do they think she'd appreciate?
Contemplate her past relationship(s). Breakups, especially difficult breakups, will cause her to revise her love map, whether consciously or unconsciously. By showing her that you are different from her ex, you'll make yourself a more desirable potential partner.
Learn what thrills her. Science has shown that the chemicals released when you and her experience fear together are linked closely with arousal and attraction. Thrilling experiences can give you both a dose of good anxiety, and set the tone for the next stage in your relationship. Roller coasters and amusement parks are a great way to get the blood pumping without actually scaring her. A suspenseful thriller can also have this effect, though you might want to avoid slasher and gore-filled films. You don't want yourself associated with the homicidal, even if you do want her heart.
Research her preferred method of exercise. The physical response you have to a workout mimics your body's response to arousal. By exercising together, not only will you both be riding an endorphin high which she'll start associating with you, but also, she'll likely see you in a more attractive light.
Winning Her Heart
Use mutual friends to your advantage. This may seem underhanded, but if you really are a good match and she just can't see it, your efforts to win her over can get a boost when supported by a trusted source, like her friends. If her friends think you're great, chances are she'll agree. This can only work to your advantage while winning her heart.
Use repetition. The more you hear something, the more you'll believe its true. This same fact will work in your favor when winning over your female friend. You don't have call every five minutes, which might put her off, but by staying in sight or being around her frequently, you'll reinforce the naturalness of your presence there.
Set the mood with soft lighting. This may seem a little over the top, and you might not want to employ something as obvious as a candlelit dinner. After all, you don't want to come on too strong. However, studies have shown that large pupils are a signal to which your female friend will unconsciously respond. Dilated pupils can be an indication of many things, but for your situation, most important is that pupils dilate when feeling physical or psychological pleasure. Going to a movie as friends or a dimly lit coffee shop and making eye contact will send her subconscious the sign that you have chemistry.
Cultivate your mystique. When you feel like you've met your perfect match, it's easy to say too much too soon. Holding back can be difficult, but by not giving her all the details, she'll find her mind wondering more and more about you, which could lead feelings of friendship to something more.
Flirt with her. This can be tricky, as every woman will have a different level of flirtation she is comfortable with. Take cues from her past relationships. What did you notice other guys did that worked? What flopped? Remember, its important to respect her boundaries, even when trying to win her heart. Compliment with a hint of sexiness. Instead of saying that she looks good, you might instead say, "If only my last date were as breathtaking as you." This way, you indicate subtly that you think you would be a good match while complimenting her. Find ways to be physically close. In all relationships, closeness is a sign of comfort and intimacy. Though keep in mind, some people need more personal space than others. Don't force closeness; find ways of naturally and comfortably coming together. The hushed atmosphere of museums makes whispering while standing close normal. Allow your touches to linger. You will need to gauge her comfort level before attempting this, as an unexpected touch can come across as pushy. But physical touch releases oxytocin in the blood, sometimes referred to as the "love hormone."
Be persistent, when appropriate. If your female friend is externally dependent, that is, if she relies on people or things outside of herself to feel good about herself, it's likely she will be thrilled if you chase after her. Be wary of coming on too strong. Many independent women consider that kind of behavior to be suffocating, which won't win you points in her book of love.
Expressing Your Feelings
Don't rush yourself. This is your friend, and even if you've been suffering with these romantic feelings for a long time, the last thing you should want is to make her feel uncomfortable. Strong emotions make it easy to get carried away; don't allow your strong feelings to compromise your friendship. Journaling about your feelings can help you feel less overwhelmed, which can be a powerful preventative for making a hasty, emotional decision. Write a personal letter. This will help you get all the things you want to say down on paper, without having said them to your female friend. Now you can think about whether these might come across as too strong; the last thing you want is to scare her away, especially if there's potential for love.
Gauge her feelings. Does she constantly want to hang out with you alone? Do you find her looking at you more frequently, or did she break up with a boyfriend for no particular reason that you know of? These can all be signals that she is becoming interested in you as more than just a friend.
Ask her friends. This can be dangerous, as sometimes friends will make decisions on their own that they feel is best for your female friend. However, if she has a friend that you are also friends with, and trust, you can get a clear read on the situation by asking if you stand a chance. Be sure you express yourself clearly:"Has she said anything about me? I really want to be the one to tell her myself, but I've been thinking lately that we might be good as more than friends."
Choose your moment carefully. As her friend, this will be a lot easier for you to determine than some stranger off the street. Pay attention to her work schedule, home life, social life, and any other factor that might be adding stress to her life or making her unhappy. You don't want these to influence her decision negatively. To give yourself the best odds, you should ask on a clear, comfortable day, when she is not too tired or stressed.
Get comfortable with your own vulnerability. Unfortunately, as uncomfortable as being vulnerable can be, this is the only way you are going to be able to express your feelings for your female friend. But you can take comfort in the fact that everyone at some point feels vulnerable, and use this to your advantage. As an example, you might confess your feelings by saying, "This isn't easy for me. I'm not the best at being vulnerable, and it's always been hard for me to put my feelings out there. I don't want things to change between us if you aren't comfortable, but lately I've been finding myself wondering about what it would be like if we went out on a date together."
Reassure her while telling how you feel. Especially if the friendship is important to you and you want it to continue even if she isn't interested in dating, it's important that you let her know this. You: "I hope I'm not making you uncomfortable by saying this, and I want you to know, no matter what happens, nothing will change on my end if you don't want it to. But I can't stop myself from feeling like there might be something more between us, and I have to know if you feel this way, too."
Express your feelings honestly. This does not mean hire a string quartet and sing out your love in front of her apartment complex. The way you express your feelings will be unique to your relationship. If she's the type that likes grand gestures, maybe the string quartet is the way to go. But remember, you are shifting the nature of your relationship, and that's a big step already. Be careful you don't say anything over the top, or jump into things too fast; this may only hurt your chances with her. Remember: communication is key to any healthy relationship.
When Should You Try This?
Try winning her over if you think she likes you back. If you're pretty sure she likes you as more than just a friend, too, there's no harm in seeing where things go. If you can help her see you as a romantic interest, it's possible love will grow from the friendship - it happens all the time. If she flirts with you sometimes, or says things like "I can always be myself with you, and no one else," feel encouraged to open her eyes to your love for her.
Try it once if you're not sure how she'll respond. If she hasn't flirted with you or otherwise shown romantic interest, you can still reveal your feelings to her. While you can't control how she'll react, you can be yourself and see if she'd consider dating you instead of just being friends.
Beware sharing your feelings if you value the friendship. She may like things just the way they are. Revealing your feelings is going to be a game changer. If she says she likes you too, the relationship will change; if she says she's not that into you, it will also change. Worst-case scenario, she won't feel as comfortable with you anymore, and she won't feel able to just go back to your normal friendship.
Always take no for an answer. Respect her feelings and her answer. No matter how much you love her, you can't make her love you back. She doesn't owe that to you. If you really care about her, don't keep trying to "win" her after she's already turned you down. Reader Poll: If you’re struggling to turn a friend down, we asked 178 wikiHow readers who’ve rejected a friend, and 71% of them agreed the best way to say you’re not interested is by being honest and straightforward, but gentle and kind. [Take Poll]
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