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10 Second Date Tips for Men That’ll Help Escalate the Relationship

By Emyli LovzFebruary 3, 2019Strategy
second date tips for men

So she’s accepted your invitation for a second date, cheers! But don’t get cocky too soon. This nascent relationship is still a fragile one, one that deserves careful planning. If you’re already infatuated with the woman you’re seeing and want to shift romantic gears, there are a few second date tips you should keep in mind. With these tips informing your next moves you’ll be more than mentally prepared to turn those embers into a full-fledged bonfire.

Tip #1: Get Moving

There’s something tribal about breaking a sweat with a romantic interest. Perhaps it transports us back millennia to when we had to fend for our lives with out close-knit nomadic groups. It may seem a bit odd, but researchers had emphatically found that moving together accelerates emotional bonds.

Sweaty palms, a thumping heartbeat, and grasping for breath are all signs of physical arousal and romantic attraction. Research participants have often confused physical arousal for romantic attraction. Though I’m not suggesting you use physiological witchcraft to trick your date into falling for you. Working out is simply a natural way to feel happier, bond with another, and stay fit.


Each date brings with it certain obstacles. One of these is that of maintaining a stimulating conversation. Should you dread the looming possibly of awkward silence you’d do well to avoid restaurants and cafes. Instead, place the emphasis of the date on the activity.

Dates based around physical activities will put the action in the spotlight instead of yourself. Let these shared activities drive the conversation instead of how awesome your Caesar salad is. Here’s a few examples from a recent article I wrote on Physical Second Date Ideas:

  • Hiking + Picnic
  • Leisurely bike ride + Animal watching
  • Yoga at the beach
  • Hit the dog park
  • Free salsa class

Tip #2: Keep That Wallet Holstered

Being a proponent of MegaDating means two things. One; you’re a prolific dater. And two; you spend a solitary hour on each first date. This means that come time for the second date you’re still basically getting to know a stranger. Doesn’t it seem odd splurging on a stranger?

If splashing a torrent of cash on a second date seems a bit far-fetched, we’re with you. Keep that money ensconced between the folds of your wallet and instead keep the date free and leisurely.

Flashing the cash on a second date may have a number of repercussions. In response to that three-course dinner- she may be more attracted to the lifestyle perks of dating you than your personality. Such a start to a relationship is the beginning of an incredibly shallow relationship that has already been stamped with an expiration date. The second reason to embark on a financially friendly date is because if you date as often as I once did you’ll need to save that money for the people that warrant spending it.

Scrambling for a free second date idea? I’ve got you:

  • Get nostalgic and play a board game
  • Explore your area with Geocaching
  • Watch the seagulls feast at dusk
  • Free museum
  • Meditation meetup

Tip #3: Make Contact

An accepted invitation to a second date means that she’s genuinely interested in you –unless you went to a Zagat rated restaurant for your first date, in which case maybe she’s just a hungry foodie. With this in mind it may be acceptable for you to engage in some light flirting by way of touch.

Continuing to go out with someone doesn’t mean that you have the right to touch them. Attraction is a fickle flame that needs the proper amount of fuel to be kept alive. Is she laughing at your jokes, making prolonged eye contact, all the while inching closer to you? If so, she is probably okay with a little light touching. I’m not suggesting you let your hands palpate the curves of her lower back. Rather, start safe and if the signs are pointing in your favor, venture to more romantic regions of the body.


Breaking the invisible barrier between the two of you is the quickest route towards escalating a relationship -but this path must be tread with caution. Make the wrong move and you’ll likely find yourself ghosted. However if you have your physical overtures accepted, you’re newfound relationship will find itself on the highway towards something substantial.

Second Date Tips for Guys #4: Ask the Right Questions

Hopeless romantics will never stop searching for the key to love. But in 2015, they thought they found it. New York Time’s writer, Mandy Carton, wrote an article with a headline that embodies clickbait, “To Fall in Love With Anyone, Do This.” Within this fool’s gold article she refers to a study carried out more than 20 years ago by a psychologist that entailed making a series of strangers ask each other 36 questions each, and concluded the ‘date’ with a four minute period of unbroken eye-gazing.

The authors of the study claimed and later vindicated their hypothesis that, “One key pattern associated with the development of a close relationship among peers is sustained, escalating, reciprocal, personal self-disclosure.”

Asking your date 36 pre-scripted questions is a bit laboratorial. The reality of dating is that it occurs outside the confines of white walls and men in lab coats (hopefully). What we learn from this study is that penetrating questions have the power to cultivate a relationship of depth. Questions of substance are classified as ones that probe and stimulate recipients. Small talk and chatter regarding your surroundings or mutual interests do well to kick the conversation off, but to escalate a relationship throw some of these questions into the mix. I’ll list a few examples here:

  • What made you go on a second date with me?
  • Before making a phone call, do you ever rehearse what you’re going to say?
  • What’s something you’re terrible at?
  • If you could give your middle school self one piece of advice, what would it be?
  • How long do you usually wait before kissing someone?

There’s no need to bring a dating cheat sheet with you. Rather, see your date as the proverbial complex onion that she is, and with care, peel back the layers and figure out what’s inside.

Tip #5: Sun Shower

Unless you were friend-zoned the second she laid eyes on you, she shouldn’t be 100% comfortable with you by the start of the second date. This means that you should still keep your date confined to public places during the daytime.

A woman won’t be willing to let her guard down if she can’t trust you. Heed this second date tip for men and earn her trust while simultaneously demonstrating your romantic side in the light of day. Once you’ve proven yourself as a worthy suitor, heat things up by transitioning from day to night on the third date.

Tip#6: Don’t Set a Time Limit

Followers of MegaDating will have only allotted an hour to their first date. There is only so much that can be learned about another from a paltry hour. Don’t be surprised if she’s mentally salivating at the chance to get to know you better by the time the next date rolls around. Clearly she’s interested in you enough to go out with you again, now it’s time to really dig under the trivialities of conversation and unearth who she really is.

To properly investigate this person, time limits must be thrown out of the playbook (at least for now). Break previous dating parameters and allow your second date to organically tick on as you and your lady enjoy each other. If the conversation is coasting, don’t hinder its progress by cutting the date short. On the flip side, if you see that she’s scratching her eyes and yawning, tell her you’ll see her soon and part ways.


Tip #7: Tell Her How You Feel (Or Show Her)

The dating coaches of old would actively encourage women to keep their lips locked up until a relationship could be expressed in concrete words such as boyfriend and girlfriend. Those coaches are largely from a bygone era, one where women were much more likely to be labeled and discarded as a result of their promiscuity. If you haven’t noticed, the 21st century woman is much more likely to follow her urges.

Don’t think that simply because you’ve only spent ‘x’ hours with this girl that she’ll reject a close-lipped secret or two.

Second Date Tips for Men #8: Recall Your First Date

The beauty of a second date is that you should already have a wealth of information to pull from the first date. Making connections between what she said during the first and second date helps build a solid foundation based on interest and respect. Ask her about that concert she told you about or expand on that joke that you made during your first rendezvous.

Broaching talking points from previous encounters shows her that you’re a good listener and earnestly care about the words coming out of her mouth. Use these listening skills to your advantage.

Tip #9: Do Not Give Her a Gift

As far as second date tips for men go, this should be a no-brainer. Yet sadly I’ve seen guys on countless occasions push a woman away by inundating her with material affection. Everyone wants to be liked, but to a degree. Infatuation after a single date isn’t sexy. Gifting a girl a present even when her feelings for you aren’t certain is a move only a 5th grader would second. Quiet that inner child and channel your more suave side.

Instead of showing your affection with products, use those feelings to give her the attention she deserves. Listen to her, ask questions, be interested. A bouquet of flowers or box of chocolates is something we can buy in a moment’s notice. But steamy affection by way of genuine social interaction is hard to come by.

Tip #10: Include Her in Your Future Plans

Have you playfully brushed the back of her neck but received no response? Does she drop eye contact just a moment before the fireworks go off? Does it seem as though she likes you but refuses to give you that unequivocal indication that she’s into you?

You’ll have to discern her actions for yourself. However, it may well be that she’s afraid of revealing her hand too soon. Perhaps she wants to be taken seriously instead of being viewed as a short-term fling.

Carving out future plans with her is a clear indication that she’s meaningful character in your life. The two-date mark is a crucial one. At this point you’ve spent enough time with her to know if the other is worth your time. Speaking freely about your interest in going to a concert or eating at a hip restaurant with her will mitigate any fear that she has of being just another number in your phone.


Still having second-date jitters? Let’s talk out your worries and find solutions. Select a time to chat and we’ll have a 1-on-1 Skype session that will address your fears and give you the mental fortitude to cruise into that second date with confidence.