Dating: when should a woman ask for a do-over

Learn how to effectively ask for a second date, according to dating and relationship experts.

Here are their insights:

“I really felt a connection with you. Would you like to go out again on Friday?”

Dating would be so much easier if we didn’t make it so complicated. What’s the best way to ask for a second date?

• “I like you. Do you want to go out on a second date on Friday?”
• “I really felt a connection with you. Would you like to go out again on Friday?”

Just be honest and straightforward. Don’t be afraid to put yourself out there. In fact, the more you put yourself out there, the more likely it is he or she will do the same.

Most of all, do not leave the timing of the second date open-ended. That sort of vagueness is an invitation to mixed signals and frustration.

Young daters are so fearful of doing or saying anything awkward nowadays that they often default to being deliberately ambiguous. They’re more worried about embarrassing themselves or getting their feelings hurt than they are about getting what they truly want romantically.

They’ll have a great first date and then follow it up with a cryptic text message that says, “We should do that again sometime.”

The person receiving that message has no idea what it means. “We should do that again sometime” could mean we should do that again sometime — or it could be just a polite way of saying, “Have a nice life.”

It’s really impossible to know. And because singles fear rejection more than they value connection — unfortunately — they’ll probably go with the “have a nice life” interpretation. Two people who might have been perfect together won’t wind up together simply due to poor communication.

Be direct and honest. Don’t play games.

If you had a great time on a first date — if you felt a real connection — tell them so and follow it up with a suggested date and time for your next date. I prefer calling to text messages simply because hearing someone’s voice is more personal.

Plus, there’s so much you can learn about people based solely on the sound of their voice. If the chemistry was as good as you thought it was, I guarantee your date will appreciate your direct approach.

Lisa Concepcion

Certified Professional Love Life Coach Dating & Relationship Expert Founder, LoveQuest Coaching

Ask while still on the first date

When you can see that there’s good rapport, that things are going really well, and you talk about what you both like to do, then suggest a second date.

Say, for example, you turn the discussion to things you like to do for fun, and they say they like bike riding or hiking, you can then say, “that can be our second date, we can go bike ride or hike and then have a nice lunch.”

If they like you, they’ll respond favorably, and you’ll line up the next date.

Communication is key

If you went on a first date and like the person and want to see them again, ask them what their schedule is like and if they’d like to go out again.

It’s important to know their interest level, and asking for a second date will bring that clarity.

Call, don’t text

We have become far too text-dependent as a culture, and nowhere does this play out more than with dating—people bond and connect through voice.

We can get emotion through voice, and psychologically you start to form neuro-pathways through hearing someone’s voice. Call them to say hello and then ask them out.

Stephania Cruz

Relationship Expert Author, Datingpilot

“I had a great time last night, and I’d like to see you again. Would you like to have coffee with me?”

Pursuing a second date can bring back the jittery feelings you felt when you asked the person you like on the first date, as you are not sure if they will accept or reject your invitation.

You are certain that there was chemistry on your behalf, but you cannot know for sure if they felt those same sparks as well. The first date, in your opinion, ended well and you would like to see them again, but would they like to embark on another date with you?

All of these thoughts and questions can cause the nervousness to reappear again. Unfortunately, there is no way of knowing whether the person you like felt the same sparks and are eager to go out on a date with you again unless they tell you directly.

Most of the time, however, they do not tell you voluntarily unless you ask.

Therefore, asking someone on a second date should be done sooner rather than later, as knowing whether they want to see you again or not will help you move forward (going on a third date or moving on to meet someone new).

Asking for a second date can be done on the same night that you had your first date (only if after the first date ended well, of course). If the date ended well and there was chemistry between the two, then ask away.

If the same night seems too soon, you can always call the next day and ask if they would like to see you again. Asking can be done directly or indirectly.

An example of a direct way is, “I had a great time last night, and I would like to see you again. Would you like to have a cup of coffee with me on Saturday?”

This approach lets the person know that you are interested in them and therefore you would like to see them again. There is no going around the bush; therefore, they have no choice but to be upfront about how they feel.

If the feeling is mutual, they will let you know after a statement like this. However, if the feeling is not mutual, you will also find out. Either way, you will be able to know which way to move forward.

If you do not want to be so direct, take what you know they like or are interested in and use it to ask them on a second date. For example, if they love ice-cream, you can say:

“They just opened a new ice-cream shop down my street. Would you like to try it out with me Friday evening?”

Asking in this way puts the focus more on the activity (e.g., eating ice-cream) versus directly saying that you want to see them, which puts how you feel about them on the spot.

“This has been a great time. We really should do this again. What do you say?”

The best way to ask for a second date is to make sure you had a great first date. After sharing some laughs or engaging in some flirtatious banter towards the end of the first date, you might say something along the lines of:

“This has been a great time. We really should do this again. What do you say?”

If the answer is an immediate affirmative one, let them know you’ll give them a call to schedule something. On the other hand, if there is a hesitation or a noncommittal response, you may have misread how well the first date went.

Another tactic is to use what you’ve learned from them about their likes and favorites during the first date or previous conversations you’ve had with them.

If they mentioned their favorite band, actor, musical, team sport, or whatever it is and you are aware of something involving their favorite is taking place, invite them.

“I just read that such and such is coming to town and couldn’t help but think of you. Would you be interested in going this weekend?”

The most important thing needed to have a second date is to establish a great rapport and ensure you both had a wonderful time on your first date.

If there was no chemistry, no ease of conversation, smiles, laughter, flirtatious banter, incidental touching/hand-holding, or a kiss goodnight, it might be a challenge.

Let’s face it; no one wants a second helping of a bad meal. People rarely want to invest time or money after having a bad, boring, or awkward first date with someone.

Asking for a second date might be one of the most nerve-wracking things that you will do in a relationship. Not being sure if they want to go on a second date has become your dilemma, but you just want to go on another date with her/him.

As a relationship expert, there are some ways to ask for a second date by just doing this two simple ways:

Be straight forward

If the two of you are still talking and you think he/she enjoyed your first date, there is nothing to worry about, and just ask them if they want to go somewhere. Nothing beats being straightforward in asking for a second date.

Try being casual

You can ask for a second date without asking for a second date literally. If both of you like sports, then try saying, “There is a basketball game this weekend, and your favorite team is playing. Do you want to watch the game with me?”

And just like that, you asked for a second date without being straightforward.

Get to know her on the first date and use that information to plan a second date

Here is what I coach men on asking for a second date: Be a man with a plan.

On the first date, you got to know her and found out what the two of you have in common. Use that information to plan a second date. If you both like to go hiking, plan a hike. If you both like jazz, find out where there is jazz music that you will both enjoy.

She will appreciate that you are suggesting doing something that she indicated she enjoys doing, and she will appreciate that you were listening when you were talking to each other on the first date.

It makes her feel special.

Don’t ask her to plan a hike or where to go to hear jazz. If you do that, she may feel that if you can’t even plan a date, how will you handle the challenges of marriage and family life. It will be a strike against you.

Re-open the conversation with a callback humor

In my experience, the best way to ask for a first date is to not make it seem like a big deal. Don’t call it a date or wax lyrical about how you’d love it if they came along; just invite them somewhere.

Brevity makes people less nervous about accepting your offer.

This approach works well for the second date too. I like to re-open the text conversation with callback humor, anything that reminds them of how awesome the first date was.

It could be a throwback to a funny joke or a cheeky remark about something cool that happened. If you took funny photos on the date, you could send them. These types of messages create an emotional impact and are easy to respond to. All it takes is “hahaha.”

From there, go ahead and suggest something else you can do together. You likely discussed something on the first date that gave you a good idea for a second one.

You don’t have to make small talk over text before asking them out. Save that for when you’re together. Just send something funny to reopen the conversation. If they respond, go ahead and invite them somewhere awesome.