Whether you’ve been attracted to her for years, or you only developed feelings recently, asking out a woman you are friends with can be an extremely nerve wracking experience. You value her as a friend, and you don’t want anything like hurt feelings clouding the water. If she says no, things will probably be awkward for a little while, maybe a long while. If she says yes, there truly is no going back; if you two do develop a relationship, it will all be over if you break up, leading to no relationship and no friendship. However, friends can make the best romantic partners, and is the basis for a relationship that most often leads to marriage. There are good arguments in favor of taking the plunge, and three tips for how to do it.
Step One: Decide If You Really Want and are Ready for a Relationship
This is a big deal, because things just can’t stay casual between two people who know each other well. You already have a bond of friendship; layering romance and sexuality over that is going to make a strong tie very soon. Nothing good will come of this if you try to back out when things get intense. You don’t have to be sure you want to marry her, or anything extreme like that, but you should be ready at least for an exclusive dating relationship before you set things up.
Step Two: Assess Whether She is Available
If the woman you want to date is saying things like she’s ‘just not ready for a serious relationship’, etc, then you should believe her. This is also not a guide to steal someone’s girl. If she is in a relationship then she is not available. Assume this even if she’s not happy with the relationship; you don’t want to start the foundation of your relationship with bitterness over her and some other man who didn’t treat her right. She has to be unattached.
Step Three: Ask Her Out in a Low Pressure Way
The temptation here is to go all out. After all, you know her well and you know what she likes, right? As romantic as this sounds and could be, it’s also an all or nothing maneuver. If you hire a sky writer and then show up with two dozen roses and a gilded invitation to a fancy restaurant, that’s a very high pressure technique. There’s really no failsafe; either she’s touched and agrees, or she’s forced to say no to a very extravagant display—and that just makes it awkward. The better approach is to ask her to an event you know she likes. Be upfront that you’d like it to be a date, but don’t try to read her a sonnet or anything. That way, if she refuses, you can back down graciously and let the whole thing blow over.
Nine times out of 10, it’s worth the risk to ask out a friend. If you have the right timing and the right approach, you could get one of the best relationships of your life. If you never take that risk, she’ll go away.