On a weeknight, go to places that give people a reason to be out: trivia and quiz nights, live music and open mics, karaoke, comedy, wine bars, hotel bars and small neighborhood bars after work. Fewer people are out on a Monday, Wednesday or Sunday night, but the girls who are out chose to be social, and in a quiet room with no lines you can actually hear each other. Thursday is the busiest weeknight and the easiest place to start.

Why a quiet night can be a good night

Men tend to write off weeknights because the rooms are half empty. That misses what a quiet night gives you. Fewer guys are out competing. Conversations last longer because nobody is shouting. And the women you meet have no big plan they are rushing off to.

a dating coach likes to bar hop through small, cheap bars midweek for exactly this reason. A girl who is out on a weeknight, he says, wanted to go out and meet people, and she rarely has anything more interesting planned than talking to you. Staff are freer too. He notes that a bartender or cocktail waitress who is swamped on a Friday is wide open on a Tuesday or Wednesday.

Monday and Tuesday

The start of the week is the quietest, so go where something is happening:

  • Trivia or quiz nights. Join a team or chat with the one at the next table between rounds.
  • Karaoke. Everyone is cheering for strangers, which makes talking to them easy.
  • Open mics. Small rooms, a friendly crowd and natural breaks between acts.
  • Industry nights. Many bars run a night for restaurant and bar workers, who often have Sunday or Monday off. That crowd is social and out late.

Wednesday

Midweek has more going on. Wine bars and cocktail bars run specials, live music venues book smaller acts, and comedy clubs fill up. Run clubs often end at a bar or brewery, and most of them welcome newcomers. A Wednesday at a wine bar with a good counter is one of the easiest evenings to start a conversation, because people are sitting close together and the music is low.

Thursday

Thursday is the bridge into the weekend. After-work crowds stay out later, neighborhood bars fill up, and plenty of people treat it as their main night out before a weekend of other plans. If you are still getting comfortable approaching, start with a Thursday evening in a smaller bar. It is busy enough to give you options and calm enough that you can hear her.

Sunday night

Sunday nights are slow, but not empty. Look for bars with live music or a game on, restaurant bars, the industry crowd starting their weekend, and anywhere with an outdoor terrace in warm weather. People are winding down rather than gearing up, so keep it relaxed. Sunday is also a good night to set up a date for later in the week with someone you meet.

How to approach in a near-empty bar

A quiet room changes the mechanics a little.

Everyone can hear you, so speak at a normal volume and keep it friendly. Being heard by the bartender and the couple at the next table is fine if you sound like a relaxed person saying hello. Bring the bartender into it: chatting with the person behind the bar makes you look like a regular and gives you an easy way to include the woman next to you.

Keep the opener plain. "Is it always this quiet on a Monday, or did everyone else get a memo we missed?" works because it is true and it is about both of you.

If she is not interested, leave gracefully. In a small room, everyone sees how you handle a short answer. A smile and "enjoy your night" keeps the room on your side. Then do what a dating coach does: finish your drink and try the next bar.

Plan for your schedule

A weeknight only helps if you can keep doing it. Go out early, set a time to be home, and pick the night after which you can still function at work. One weeknight a week, every week, will teach you more than one big Saturday a month.

Practicing with a coach in the field

Small rooms are a good place to learn, and a coach beside you makes it faster. A Cold Approach Bootcamp is fully in the field in Miami and New York, with night game in bars and lounges mixed with daygame to suit you. Each training day is two four-hour blocks, with live coaching on every approach and feedback after every set.

Group runs three consecutive days at a 3:1 student-to-coach ratio, and Private is 1-on-1 for one, two or three days. Total beginners are welcome, and you leave with a written practice plan.