Okay. So you’ve finally worked up the courage to approach the woman of your dreams. You planned everything out, and are about to set your plan into motion, when you find that she (not surprisingly) has a friend (or two, or five) with her. “What do?” It depends on the situation, if you’re at a bar with a small group of friends consider the following:
- If she has one female friend: This is nearly easier than approaching her solo. Bring a wingman and approach the situation as if it were a solo mission, but instead of opening up with an introduction, ask them how their night is going. You can then set into motion any plan you and the other half of the dynamic duo may have schemed: Whether to separate the mark by having the wingman ask her friend to dance, or have the wingman distract her friend by being increasingly engaging in a one on one discussion.
- If she has her gay best friend with her: Go Solo. You’re going to have to charm both of them. You’re approaching a group, so don’t start with an introduction: Opt for something like “How’s the night (or day) going for you guys?” Don’t worry about the man hitting on you; they have a sixth sense when it comes to deducing one’s orientation. Focus on gaining his approval, which is quite easy. Converse with him, and buy him a shot: He is a guy after all.
- If she has two female friends: This can be approached different ways, but the best way to get her attention is to bring one friend and you guys focus on her friends. This accomplishes two things: You get the approval of her friends and the woman starts wondering why her friends are getting more attention than she is. If you have the confidence to believe you deserve her she will too. In all situations you want her to be presenting herself to you. To gain more of your attention she will do just that.
- If she’s the third wheel: You’ll get no resistance from the couple she’s with (most of the time). The only thing you have to be cautious of is your entry. If you can, try to approach her without drawing too much attention from the couple (i.e.: don’t approach her during their conversation, like you would two girls). If you can engage her in conversation and have smiling, the couple will most likely leave you two alone.
- If she’s a bartender: This will take discipline. You’ll want to lay groundwork early: Make a joke, smile, and present yourself as “not just another drunk guy hitting on her.” Don’t tip her too much, but just enough to get her to notice (25% should suffice). Your only goal in the early stages of the night is to make sure she remembers who you are. She’ll remember the guy that made her laugh, orders a round of drinks through her, and isn’t hitting on any other girls that night (remember what I said about discipline?). It goes without saying you shouldn’t get too drunk. A two-drink buzz works wonders for any situation on this list. Before you leave, ask her what she’s doing the next day. If you’re active, invite her to join you on your jog or walk. Most bartenders are fit (and gorgeous), and would embrace an active date as opposed to something like coffee. Going for coffee is a solid date as well, but play it by ear: If you think she’d be open to both, go for the active date.
- If she’s in a group setting (4-6 people, more girls than guys, and you know none of them): You’ll need a female wingman for this one. This kind of approach should be done in two phases. Use your judgment and determine if the group is clique-ish. If you can gauge from their body-language that they’d be open to friendly engagements, you can start the first phase. Approach the group and give them this scenario: You and your female friend are arguing about (insert funny argument here). You two decided the best way to settle it was to take a poll, and the loser will buy the group a shot. The result of course is rigged: You’ll exclaim in defeat regardless of the poll result and buy the group a shot (hope it’s happy hour!). Thank them for participating afterwards and introduce yourself before leaving. After you leave they’ll talk about how fun / nice / cool you are, thus boosting your profile to the woman you’re after. A while later if you can catch her solo, or in a situation similar to the ones explained, you can approach her, converse, and get her number.
Everything may not go as planned! Mishaps from credit card declines to “intervening friends” plus: What I did when I accidentally spat the mint I had in my mouth onto my shirt where it remained clearly visible – will be discussed in the final part – What to Do When Things Go Wrong – coming [12/7/12]