How To Ask For A Second Date

Gay Dating

How to Ask for a Second Date (3 Tips from a Gay Matchmaker)

Anthony Canapi

Written by: Anthony Canapi

Anthony Canapi

Known in the matchmaking Industry as California’s Gay Matchmaker, Anthony Canapi is a Certified Professional Matchmaker and Founder of Best Man Matchmaking, an old-school, personal LGBTQ+ owned matchmaking company for gay, bisexual, transgender, and queer+ men seeking a long-term, committed relationship. Mentored by celebrity matchmakers, Anthony has connected more than 1500+ professional singles for the past 9 years. Anthony's goal is to help as many GBTQ+ men find love in an offline, safe environment by introducing them to quality singles.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

Discuss This! Discuss This!

Picture this: You’re on the first date, you went out to a nice restaurant, or met up for an outdoor activity with your date. Either way, you come to the realization that you’ve met a really great guy and you want to see him again.

He’s the type of man you see yourself with. Perhaps you have similar interests, his presence or energy makes you feel comfortable and safe, or maybe you’ve finally found someone who’s the top bunk to your bottom bunk (we’ve all been there, bottoms), at the end of the day, you want to get to know more about him on a second date. 

Here’s the catch: The date is wrapping up and neither of you is bringing up the possibility of a second date. The fear of rejection, nervousness, and/or getting in your head, quickly heightens. 

The first date is ending: Do you try to bust out a move to indicate you had a good time? Do you go in for that hug or kiss? Do you ask for his phone number? Do you tell him right then and there that you want to plan a second date at his earliest convenience? What do you do?

As a Personal Matchmaker for nine years, I’ve had gay, bisexual, transgender, questioning, and queer date coaching clients commonly ask me after their first date is: How do I ask for the second date without it being weird?

When matchmaking clients work with me, I play as the middleman. I send a date feedback form for both daters to fill out. If both daters want to see each other again, I initiate the second conversation for planning Date #2. If one or both daters feel a platonic connection, I let their match know, and move on to the next match. But without me holding your hand, as a gay man myself, I totally understand the built up nervousness when asking for that second date- I mean, let’s be honest: Rejection hurts a man’s ego, whether you identify as GBTQ+ or straight.

Most gay men I work with think it’s rocket science to get from Date 1 to Date 2, and I can tell you right here and now that’s not the case whatsoever. Want to nail down how to ask for that second date like a pro? Follow these three tips. 

1. Be Genuine & Straightforward

I’m going to tell you something that may shock you: Gay men are just like any other men (gay gasp!). Gay men are not Martians; we’re not wired differently just because we like the same sex. There’s no “Alyssa’s Secret” code to crack to get the second date. The fact of the matter is this: Communication and honesty are the best way to date no matter who you are. 

If you had a great time on the date, let your date know! A simple, “I had a great time tonight”, will calm all your nerves and push away all of the negative thoughts and what-ifs you had in your head.

Sometimes, single men, regardless of sexual orientation, need that confirmation from our date as it keeps our nerves in check. Most of the time, we tend to be our own worst critic when we think that the other person was not satisfied or that we didn’t meet their expectations. We then put the blame on ourselves and ask, “What did we do wrong”, thus creating a fantasy that’s not reality.

Gay Dating Sites Black Men
Keep a positive attitude when building a new love connection.

After you state that you had a great time on your date, don’t be afraid to follow-up with, “I would love to see you again.” Naturally, this gives your date the opportunity to give a nonchalant answer.

  • If he responds that he would love to see you again, it’s crucial for you to exchange phone numbers toward the end of the date so you both can follow up the next day via text.
  • If he doesn’t respond with a concrete yes or no, don’t take it personally or think negatively of it. Simply follow up again that you had a lovely time on the date, and ask to exchange phone numbers and send him a text the next day.

After exchanging phone numbers, most of my date coaching clients ask the big ol’ question: Do I give them a hug or kiss after the date to end the night strong?

It’s going to sound cliché, but many of my clients have found success for the past nine years with the advice I’m about to impart: After exchanging numbers, if you’re smiling or getting all giggly with your date,there may be a moment when you are both just looking at each other. Maybe there’s an instance when one or both of you look at each other’s lips — GO FOR IT! If there’s no eye contact being made and/or if there’s this awkward laugh/silence being thrown back and forth, do the bare minimum and go in for a hug.

You’re not obligated to either kiss or hug at the end of the first date, but let’s be honest: Men are visual creatures with a lot of testosterone. The only thing I have to say is do not have sex after the first date — but that’s a topic for another post.

Once the first date hits success, that’s only a third of the battle. Step 2 will really determine if the second date is a go or not.

*Note: If your date is all in for planning Date #2 on the spot, skip to Step 3!

2. Follow Up Via Text

Most of my date coaching clients fall into the same problem of “The Waiting Game” in their text conversations. They are waiting for the other person to reply or say something first. Sometimes, men feel that they come off too strong or too eager if they follow up the next day. They may feel that their date needs to follow up first.

Unless you’re texting him at 6 AM in the morning or sending multiple texts one after the other, you’re not being too strong or too eager. You’re initiating a new conversation.

Once again, communication and honesty go light years. You don’t need to initiate the conversation with a long paragraph, nor do you start the conversation off with a one-word conversation starter.

All you have to say is this: “Hey, I just wanted to let you know that I had a great time last night and I would love to see you again. How does your schedule look this week or next week to go on a second date with me? Let me know.” Maybe add a smiley emoji to be flirtatious.

After that, LEAVE IT ALONE!

Some men feel they need to have an answer to feel closure or at the very least, they feel it would be nice if they responded back as it shows that they’re a man with courtesy and not a f-boy.

Here’s the truth of the matter: Some people are just going to ghost you, and some dates will not reply back to you instantly. It’s unavoidable, and it will happen in your dating journey from time to time. It’s not going to become obsolete as people do naturally forget or are just plain rude and will ghost you. Again, it’s part of the dating process.

At the very minimum, if you feel the need to follow up one more time, use the 24-hour rule: Wait 24 hours after sending the first follow-up text and reply with, “Hey, just wanted to circle back and make sure this didn’t get lost in the mix.” After that, LEAVE IT ALONE!

Sooner or later, he will reply back (yes, it can happen), and if he doesn’t reply back, let it go, take it for what it is, and move on to the next match! Once he does reply back, hit the final nail in the coffin.

3. Plan the Date or Move On

If the feeling is mutual and he wants to see you again, you’re in, but you can’t keep him hanging: Get the second date in the books!

Once he replies back to you, it’s a courtesy on your end to reply back the same day, or at the latest by the next day, to Plan Date #2. This will show him that you’re just as interested in going on another date as he is.

When planning Date #2, find a hobby or interest that both of you have in common, and use it to plan the second date. The options for Date #2 are limitless: exploring an art exhibit, going to a food festival, exploring a pier by the beach, going to an escape room, going to a restaurant you both like, taking a stroll around a park, etc., the possibilities are within reach.

As much as I would love to wave my magic wand and have every reply end with a happy ending, some cases are not as easy as that.

Photo of a man texting
His texting style after a first date will indicate if he’s open to a second date.

Sometimes, you will be in a position where he comes to his own conclusion, which is: He found the date to be platonic and would like to be friends or not go on a second date with you.

It’s crucial for you not to take it personally or to ask yourself “why” or “what did you do wrong.” You did nothing wrong. The other person just didn’t have a romantic connection with you and THAT’S OKAY, it’s part of the dating process and you can’t force someone to like you; if dating were so easy, everyone would be in relationships.

All you have to do in this scenario is take it as it is. Reconfirm you had a great time on the date, wish them well, and move on to the next match! If you found this person to be a great guy and you would like to keep in touch platonically or he wants to keep in touch platonically as friends, follow up with, “I would love to keep in touch” or “I would love that.” 

Take a Breath & Just Go For It!

Dating is a process even at its highest moments. You can’t start at Point A and skip to Point D, you have to go through A, B, C to get to D.

You’re on the first date, and you come to this realization: This man you’re on the first date with is actually a good guy. 

It’s natural that we’ll get anxious or have the moment get the best of us. But if you start using these three steps, whether the response ends with a rose or you going home, asking for a second date will be a walk in the park.

You like that man you just went out with, ask him out! You know how to do it now!