Sitemap
7 min readOct 12, 2021

--

For Men: First Meetup Advice and Etiquette (With Women)

I’ve been on a lot of dates this year via online dating. Some good, some awful, and a lot of meh. One thing a lot of even the good dates were lacking was some common-sense etiquette from my male dates. So I figured I’d write up a little something that might help you guys navigate that first meetup date a little more successfully.

1. Boundaries & Expectations. Good place to start. So you swiped right or clicked the heart or whatever, and you match. You might have even chatted her up a bit. Then she states (or you read in her profile) that she’s looking for monogamous dating or exclusivity, whereas you might be looking more for casual open-ended dating, FWB, or a hookup. Or maybe it’s vice versa. Either way, you’re heading for trouble already because you have different expectations from the start.

So what does monogamous dating/exclusively mean these days anyways? Let’s discuss. Someone looking for this kind of relationship isn’t necessarily looking for commitment right off the bat. It just means you are only focusing on just each other, not throwing other people into the mix, as you continue to get to know each other and consider whether you are a good fit for each other. You are still free to walk away from each other at any point; you are just exploring the relationship without the distraction of other potential suitors waiting in the sidelines and taking away from the budding relationship energy.

If one person isn’t willing to participate honestly in this endeavor, it’s not fair to either of you. At this point, it’s better to agree to terminate the match and look for someone with the same expectations as you. Otherwise you run the risk of one person feeling trapped in a situation they don’t feel comfortable in, or someone feeling like they are being forced into a more casual relationship than they are comfortable with. Don’t waste each other’s time if there’s a clear expectations mismatch. You aren’t going to change the other person to fit your needs.

Make sure you are honest and establish clear expectations for what you are looking for right off the bat, and are both on the same page. This would have saved a lot of dating trouble and heartache for a lot of people I know, including myself.

2. Presentation. When you get ready for your meeting, even if it’s to a casual location, make some effort to clean up and wear decent clothes. Don’t show up looking (and smelling) like you just came from volleyball practice. I guarantee you the woman will be putting some effort into doing her hair, makeup, and choosing an outfit no matter how casual the venue, so you should make a little effort to look (and smell) nice too. Don’t forget to brush your teeth! (That’s a story for another blog post).

3. Conversation. This can be a game-changer, or a date-killer. Before you go out to meet your date, have a list of things you’d like to ask her ready to go, either mentally or written down. Yes, you want the conversation to flow naturally, but there will always be some places where there are awkward silences. That’s when having some questions handy that show interest really help. If you’ve chatted a bit online or over the phone, try to expand on topics you’ve already discussed to deepen your connection. If she’s shared personal details or information about interests, ask for more details. Express interest in her work or hobbies. Find out if you share common ground on things like politics or religion or favorite shows or movies or music or other interests. Ask her what she’s passionate about, what are her goals and dreams.

The worst thing you can do is just sit there and either not talk, or talk so much she can’t get a word in edgewise. I’ve had both of those experiences and they were painfully awkward and not enjoyable. If you see your date looking away a lot off into space, sitting with her head on her hand nodding but not talking much, she’s probably bored and thinking of ways to politely leave. You can still salvage things even at this point by apologizing and bringing her back into the conversation. It’s understandable to get nervous at a first meeting — blame it on that and do your best to recoup.

Make lots of eye contact if you are really feeling a connection. If appropriate, you are feeling genuine attraction, and the conversation lends to it, try and make light physical contact. I’m not talking groping under the table or grabbing her butt; I mean touching her hand across the table, or lightly against her arm or back for a moment. If she’s into you, she’ll lean into it. If not, she’ll pull away. Even if she pulls away out of surprise she still might smile to let you know it was appreciated even if she wasn’t ready for it. If you get the stink eye in response; well, safe to assume she’s not feeling the attraction. Apologize, cut your losses, and unless she initiates further conversation that might be the end of the date.

Worst case scenario, you meet someone you honestly just don’t click with and don’t have much in common with. It’s ok to laugh and be polite about it end the date nicely by saying something like “I guess sometimes opposites don’t attract, it was nice to meet you but I think we might both be wanting to end this before it gets any more awkward” and shake hands, smile, and part. Don’t just duck out the back- she still made an effort to meet you. The least you can do is part politely.

4. The Bill. It’s a nice gesture to offer to pay, but most women these days are comfortable splitting or paying for their own part on a first meeting. This way she don’t feel any obligation to you. So if she insists on paying her part, it may make her more comfortable to so do, so let her. If she offers to split things right away, same thing, let her. If you offer to pay and they accept, well, that’s your choice and don’t judge her for it or expect anything from her because of it.

On the other hand, don’t make a big deal about insisting to split the bill. It’s ok to just ask nicely “are you comfortable splitting the bill?” without a lot of drama and a story about how women are just out to get free stuff from men these days. Or something about how women should pay if they are really feminists. That kind of behavior is not going to win you any points, just unmatched and blocked.

And you grifters out there, we see right through the stories about losing your job recently, or unexpected car accident, stolen wallet yada, yada. If you don’t have the money to go out on a date, don’t go out on a date. We might pay for it just to end the date, but most likely you’ll not hear from us again.

5. Parting. If the date went well, and there was lots of eye contact and smiling, and some physical touch, offer to walk her to her car. If she says no, that’s that, hopefully you’ll hear from her again and tell her how much you enjoyed her company. Do not get butthurt if this happens to you at this point. Many women I know have been assaulted by seemingly nice guys walking them to their cars. It’s not necessarily about you, it’s about her level of comfort with someone who is still basically a stranger at this point. Respect that.

Ask if she’s comfortable with a hug before she leaves, otherwise a gentle handshake. Don’t make it creepy. Again, I’ve had great dates up until this point get ruined by a guy who groped me uninvited in the middle of a coffee shop in broad daylight. I’m not talking about a simple hug, it was a hand up my shirt horribly inappropriate thing. Another time one guy followed me out to my car, uninvited, and rushed in to try and kiss me so that I had to push him off me. Don’t be those guys.

If she does ask you to her car, and you continue to talk, and she initiates closer physical contact, that’s when it’s ok to make a move to go for the kiss if you are feeling it.

6. After the Meetup. This is almost as important I feel as #1, and yet almost never happens these days. Whether your date was good, average or ugly, have the common courtesy to contact the person and thank her for taking the time to meet with you. If you weren’t feeling the vibe, be honest and say just that and wish her luck. Give her time to see the message before you unmatch.

If you aren’t sure if she was into you after the meet up, send the same message just thanking her for taking the time to meet up, and adding that you had a good time and really enjoyed meeting her. That gives her the option of replying to tell you she either wants to see you again or just wasn’t feeling it.

If the stars aligned and you ended the meetup with a nice kiss, don’t play the waiting game. Send her a message when you get home telling her how much you enjoyed meeting her, how nice the kiss was, and are looking forward to seeing her again and getting to know her more. Leave it at that and wait for her to reply. Leaving a woman hanging for days with no message after a first meeting like that is just kinda cruel, and feeds into insecurities for no reason.

I hope someone finds this helpful. Guys and gals, feel free to disagree, discuss further, share first meetup stories, or add more advice in the comments!

--

--

Responses (4)