How to Ask for a Double Date

Ask her in one short, casual line, with a specific plan and a friend you trust to be easy company. "A friend of mine and his girlfriend are going to that taco place Friday. Do you want to come with me?" is a good example. Do it after you have already been on a date or two alone, because a double date is a poor way to meet someone you met last week.

A double date takes pressure off the two of you. There are four people at the table, so silences cost less and the conversation has more places to go. A woman who is nervous about being alone with a man she barely knows will often find a double date easier to say yes to.

It also shows her your life. She sees how your friend talks to you, how you treat the waiter, and whether the people around you seem to like you. Women pay attention to that.

Wait until you have been on at least one date together and it went well. Asking a woman you have only messaged to come on a double date puts her in a room with three strangers on her first meeting, which is harder than a coffee with you.

The second or third date is a good moment. By then she knows you are not a risk and wants to see more of your life. If she has already met a friend of yours by chance, even better.

If she is the one who brings it up, say yes and take it from there.

The friend matters more than the restaurant. Pick someone who is relaxed, who treats his partner well, and who will make her laugh. Do not choose the friend who dominates the table, tells stories at your expense without warning, or has been drinking since four in the afternoon.

Tell your friend ahead of time what the evening is for. A short message works: "I am bringing a girl I like on Friday. Go easy on the old stories." A good friend will do the rest.

If you do not know any couple, a double date can also be two friends of yours, or her friend and your friend. Let her suggest someone she would like to bring. That makes her more comfortable and shows you are flexible.

Keep it light, specific, and easy to decline.

• "Some friends of mine are doing dinner Saturday. I would like you to meet them. Want to come?"
• "My friend Jake and his girlfriend invited me out on Friday. I would rather bring you. Are you free?"
• "Do you want to do something with another couple sometime? I think you would like my friends."

Notice what each one has in common. It names a plan, it says why you are asking, and it gives her a clear yes or no. It does not apologize or hedge.

Skip: "This might be weird, but..." or "No pressure if you would rather not." You can make her comfortable without announcing that the idea is awkward.

Pick a place with a short wait, a menu everyone can order from, and room to talk. Dinner, a casual bar, bowling or a board game place all work. Avoid anything loud enough that people cannot hear each other, and avoid anything that goes on for hours.

Tell her who is coming, where, and when. Give her a clear way to arrive and leave without relying on you. This is a small thing and it matters. A woman who knows she can get home on her own will relax.

You are still on a date with her. Do not spend the evening talking only to your friend. Sit near her, ask her about her day, and include her in jokes. Let your friend and his partner carry some of the conversation while you pay attention to her.

Watch how she handles the other people. If she is warm and funny with them, that is a good sign. If she is quiet, give her a way in by asking her something she knows about.

Keep your drinking moderate. A double date is a poor place to be the loud guy.

Message her the next day. Tell her you had a good time and mention one specific thing, such as a joke she told or something she said to your friend. Then suggest the two of you meet on your own: "That was fun. I would like to take you out just the two of us this week. Thursday?"

A double date is a step toward time alone together, and the best ending is a plan for the next one.

Take it lightly. She may not want to meet your friends yet, or she may not be sure about you. Say "No problem" and offer a plain date instead. If she keeps turning down every suggestion, that tells you what you need to know, and you can move on without a speech.