Stay relaxed, be friendly to the friend, and plan to get time alone with her later in the date instead of at the start. A woman who brings a friend is usually uncomfortable, not uninterested. On our coaching calls the standard advice is to say you would prefer 1-on-1 but you are fine with both, and that single sentence often means she turns up without the friend at all.
What it means when she brings one
Our coaches read it as a comfort problem. She is not sure about the date, or about you, and a friend makes it safer. That is different from a woman who has lost interest and wants a way out.
This matters because your reaction decides how the date goes. A man who looks annoyed confirms her worry. A man who is easygoing about the friend shows her he is not desperate to get her alone, and that makes her more comfortable with the idea of being alone with him later.
If she asks before the date
When she texts to ask if she can bring a friend, our coaches teach a reply along these lines. You would prefer just the two of you, since you do not know her friend. But you are happy for her to come, and you will keep them both entertained.
You are stating a preference without making it a condition. The fact that you are fine with it says a lot about you, and offering the option often removes her need for it.
A second approach works when you have a good friend of your own with comparable skill. Tell her you may be hanging out with a friend earlier that day, so you could all meet together. Now she has someone for her friend, and you have not made her choose.
Pick that friend with care. In a double date that one of our coaches reviewed, he was more worried about the man with him than about himself, because if their date goes badly, yours will too. You do not want a partner who stands around and makes the table awkward.
Introduce yourself to the friend first
If the friend arrives and treats you like a stranger, that is on you. Our coaches' rule is to take responsibility for it. From her point of view you are a random man, and she may reasonably think you are a creep. You are the one who changes that.
Say hello warmly, give your name, and include her in what is going on. This is the same charm that got the date in the first place. It moves you from invisible stranger to a friendly person at the table. That is often the difference between the conversation continuing and ending.
If you can, ask early who else is coming, so you are ready for the friend and she does not surprise you.
Plan the time alone, and do not force it
The aim is not to get rid of the friend. It is to get some time alone with her while the friend stays comfortable.
In a double date our coaches reviewed, the woman had brought her younger sister. The coach sat apart from her at first, and then got up to sit next to her. He says it was a little awkward, but less awkward than staying apart for the whole date, so you accept the short awkward moment to avoid the long one.
He also decided not to get physical in front of the sister. The older sister was clearly looking out for the younger one and probably did not want to be judged in front of her. So he took the woman aside for a few minutes of time alone, then came back so the sister felt at ease.
When the sister wanted to stay close, the whole group moved to a different part of the bar and onto a couch. That gave the date a new setting and kept the sister in sight without cutting her out.
If it is a short visit with a friend
Sometimes she cannot leave the friend, for example when the friend is staying with her that weekend. One of our coaches describes two ways to handle that.
You can suggest a quick drink with her and the friend, and say that you and she will take a proper date another time. Or you can offer to hang out as three for an hour or two, and then ask the two of them to give you and her a while to talk when she no longer has someone to entertain.
Both keep the pressure off. If you treat the friend well, the next plan is more likely to be a solid one.
When she will not do 1-on-1 yet
A student of ours could not get a nervous woman to agree to a 1-on-1 date. So he invited her out with some friends of his. She came and brought a friend of her own. They flirted and spent time together, and that gave him a much better chance of a 1-on-1 plan later.
If she keeps suggesting groups, treat it as a step. A relaxed evening with her friend nearby can get you to the date she is not ready to make yet.
Written by Matthew Stevens, Co-Founder & Head Coach. More than half a decade coaching men across the US and worldwide.
Everything here comes out of real coaching work: the approaches, dates, texts and profiles we go through with the men we coach.