Gay Dating Advice — 3 Tips for the Second Date

So, you went on a great first date, and now you’re wondering what happens next. Here comes the pivotal step in keeping the excitement strong and perpetuating — the second date. In my opinion, it’s best to always meet a new love interest within a week’s time of your first date. Otherwise, things just fizzle, and rightfully so. If your schedule is tight, plan in advance, and don’t forget to check in with your date in the meantime.

If you’ve made that effort, and there’s no return on your investment, kindly say “thank you, next” to that person. My feeling is that if a person can’t achieve a simple task of planning a second date within a reasonable amount of time, either their life isn’t in equilibrium, or they’re just not interested.

One time a client asked a matchmaking colleague of mine: “Why does he say he always wants to hang out, but he never makes plans?” My colleague’s answer was quite frank and candid: “Because he’s dating someone else who excites him more, and he has you on reserve just in case he needs the validation of being wanted.”

I feel this answer is so important when creating a proactive gameplan of getting to know a man after the first successful date. Here are three tips for gay men seeking a second date:

Something I always feel is huge in that initial positive connection is your lifestyle compatibility. Name the top three hobbies you have that you practice at least three times a week. Oftentimes, if you’re doing some strategic sleuthing, you’ll be able to identify at least one or two of those hobbies based on the person’s dating profile photos or verbiage. These hobbies have to somewhat fit into the lifestyle of the person you are dating, or at least the person should be fine with you participating in these hobbies.

Most importantly, are you fine with this person not wanting to partake in those activities? Some of the top examples that come to mind are religious or spirituality practices, physical fitness, and travel frequency. A lot of those hobbies come down to time management or even things like socioeconomic status.

For instance, I’m perfectly fine flying coach no matter how much money I make or don’t make, and I would still do so even if I was dating a more affluent man unless he paid for my first-class ticket. I think some men might be embarrassed or even be offended that I don’t want to sit by them during the flight.

This is a great time to see if you and your date have similar hobbies.

Budding relationships really flourish when you’re participating in each other’s passions together. And comfortably at that. Show an interest in that person’s hobbies, and practice active listening from the first date forward. It can only get better during the second if you find genuine interest in those hobbies. Hopefully, the banter will seem equal in that way.

I can’t tell you how many awesome second dates I’ve had over the years that consisted of me taking someone on a long afternoon hike while having a great hour or two of conversation. Then we’d end the day with a cold beer and some “cheat meal” kind of food. An unfit person may not like that. Neither would a person who is counting every single calorie.

On the flip side, I don’t want to be stuck going to a jazz concert or a movie where the entire time it’s just us listening to music or talking and not getting to know each other better. That person may be too introverted for me. I veer toward activities that are more interactive, but that are in controlled environments where both parties can be comfortable enough to conversationally bond. Try to determine what kind of date person you are.

As soon as you meet someone in the flesh, save the more connective chatter to in-person occasions. Texting your date can be a bit transactional, and the point of dating is to create emotional ties, not send mixed messages.

Second dates are meant to delve a little deeper into another man’s vulnerability. I’m not saying you should go into your full depressing dating resumé and discuss how a certain person hurt you. I’m just saying you don’t need to be so giddy with “sunshine and rainbows.”

Texting isn’t as personal as talking face to face.

I love video calling the person just in case I’m not able to meet him again right away. Never offer hurdles, but offer solutions — it’s more attractive than you know to someone.

I feel it’s almost impossible to get a full authentic side of someone’s humor or genuineness through text messaging of sorts. Relationships shouldn’t feel so convenient. They do take work, but work that feels easy and exciting. You should care that they care to check in on you every day since that amazing first date. This isn’t asking too much because, in reality, it shows that someone can care too little.

I come from a very pragmatic and cerebral context when it comes to being aware of one’s time. Without being too domineering, it’s important to mention things that can potentially be in dealbreaker territory.

Do you prefer monogamy or polyamory? Would you be open to dating someone HIV-positive? Do you want kids? Do you see yourself living in your city and settling down there? These questions are very valid, and I feel most people would have answered these important questions naturally in previous conversations. If they haven’t, this is the perfect opportunity to lightly talk about these things.

It’s OK to start asking important questions on the second date.

I also think this is the best time to stretch people’s opinions on those topics. Maybe you’ll be the person to shed some light on a current preference he has that he hasn’t thought to see in the light you’re directing him toward.

I’ve always hated hearing people say that dating shouldn’t feel like a game. In the beginning, it kind of is. You have winners and losers. You figure that out by making the time to connect with someone — to play. If this person doesn’t seal the deal after you’ve made an effort, they are the loser. Games have rules. If the rules are mutually followed, you’ll have fun, and maybe you’ll both eventually become winners.

No one likes a person who doesn’t follow established rules or even makes up his own rules that only apply to him. That person is then not the right player for you to play with, and that is the honest game of life. Now, get to dating!