Dating questions answered: Should he pay on a first date?

Dating can be a minefield of questions and concerns whether you're on a first date, a third or you haven't even asked him out yet. That's why we're answering some of the most common dating questions with the help of some experts, starting with: Should he pay on a first date? Stay tuned for more questions later this month.

Paying for the date defines the date as an actual date, says April Masini, relationship expert behind the critically acclaimed Ask April advice column and author of four books on dating including Date Out of Your League. “If he pays for the first date, the date is clearly a date and it's not 'hanging out.' This is important so that you both understand that you're dating and not stepping into that swampland better known as the friend zone,” she explains. “When he pays for the date and picks you up, drops you off and does other things associated with dating and not hanging out, there is less confusion in the relationship.”

It happened to her: "I once went out with a guy a few times, to a bar for a few drinks and then to a movie and we each paid our own way. It turned out that this guy wasn't actually interested in me, at least not as more than a friend. Lesson learned. I totally take into consideration whether a guy pays to make sure he's actually into me." Tonya, San Antonia, Texas

When he pays for the first date, that gives you insight into his fiscal self, notes Masini. You get to know what he's like when it comes to spending money. “This is an important part of who he is and a great way to learn about him and to be able to decide if he's someone you want to continue dating,” she explains. “For instance, if he insists on splitting the bill, you can expect more of the same, and less generosity than you might be looking for in a relationship. Or if he's someone who's toting a Groupon and a Living Social coupon and whips them both out at happy hour where your date is virtually free, he may be someone who's always looking to cut corners.”

It happened to her: "My ex-husband was notoriously cheap. We rarely went out for dinner, vacations were unheard of unless you count his parents' condo in Florida. Looking back, he was always tight with money, even on our first few dates where he made me split the bill every time. I should have paid better attention to that fact!" Natasha, San Jose, California

Paying for the first date also shows he's invested in dating and isn't just looking for a good time (or a booty call). After all, dating is expensive. “After a guy adds up the price of dinner, the movie, the grooming expenses, the gas, the car maintenance he has to pay for to make sure he can pick you up?— it's expensive to date,” affirms Masini. “So if a guy is paying for that first date, it means he's invested in the process. He wants to spend the money because he's looking for a real relationship,” she explains. “Someone who's just looking for a good time isn't interested in investing in a first date the same way someone who springs for an impressive concert and Champagne is.”

It happened to her: "I honestly don't mind chipping in for a date. I'm not one of those women who needs car doors opened for her or flowers every other day. But it really does feel like someone cares about the outcome of a date when they pay or at least offer to pay. It's not the be all and end all, but it can speak volumes about how interested someone really is." Bethany, Newark, New Jersey

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Dating questions answered: How do I know if he likes me?

Dating can be a minefield of questions and concerns, whether you're on a first date, a third or you haven't even asked him out yet. That's why we're answering some of the most common dating questions with the help of some experts. This week we're talking about how to tell if he's into you.

Even after you've gone on a few dates with someone, it can be tough to tell whether a guy you're seeing is genuinely interested. We asked relationship expert, matchmaker and love architect Kailen Rosenberg for her tips on figuring out if he's truly into you.

If you're dating a guy that only talks about himself and never seems to ask you any questions, he might not be as into you as you hope. “It's a good sign if he asks about you, your day and the things that interest you and are of importance to you,” says Rosenberg.

It happened to her: “I can totally tell if a guy is into me based on how much he actually listens. If I'm telling him about my day and he's texting or not bothering to ask questions, it's probably not going to work.” Amanda, Tallahassee, Florida

Texting is probably the most common form of communication, so of course, any guy you meet will be texting at some point, but he shouldn't be doing it all the time. “Even if he still texts, it will be to show you that he's thinking of you,” says Rosenberg. “He'll call to hear your voice and to ask you out for that next date.”

It happened to her: “I stopped seeing a guy last year because I could never get him on the phone. He would only ever text me, which is OK for making plans and stuff but sometimes you just want to hear someone's voice.” Deena, Salt Lake City, Utah

There's no denying sex is fun and a great part of any relationship, but if all he cares about is sex, he might not be relationship material. What you want to see is someone who's willing to wait, says Rosenberg. “Although he could be dying to get you under the sheets, he's more interested in taking it slow.”

It happened to her: “My husband and I actually didn't sleep together for the whole first month of our relationship. It seems like a long time, but I really feel like we connected on so many other levels before getting physical.” Trish, Portland, Oregon

When it comes to dating, there might be countless rules about when you're supposed to call, but all that just complicates things, says Rosenberg. “When a man is interested, you know. He doesn't wait around to call and he doesn't play games,” she explains. “Bottom line, he can't wait to hear your voice.”

It happened to her: “I hate when guys play games and sit around waiting to call. If you like me, just tell me. Some of my friends think it's weird when a guy they meet calls right away, but why shouldn't he? He's just being upfront, which I think is cool.” Fiona, Buffalo, New York

You can definitely tell if a guy is truly into you when he starts making plans that go beyond, “Hey, want to come over tonight?” “I'm not talking marriage but I am talking weeks out for upcoming concerts, plays, art openings, anything,” says Rosenberg. “He's already thinking into the future.”

It happened to her: “I knew my current boyfriend was going to be more than a quick fling when he surprised me with concert tickets for a show that was three months away!” Kris, San Antonio, Texas

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Dating questions answered: How soon is too soon for sex?

Dating can be a minefield of questions and concerns whether you're on a first date, a third or you haven't even asked him out yet. That's why we're answering some of the most common dating questions with the help of some experts. This week we're talking about sex and how soon is too soon.

“If you have sex before you're ready, you'll ruin the chances of developing the relationship further, and you're setting yourself up for a really awkward morning after,” says Tina B. Tessina, Ph.D., (aka "Dr. Romance") psychotherapist and author of The Unofficial Guide to Dating Again. She shared a few more reasons to wait for?— rather than rush into?— sex.

When you decide to become intimate with someone is an important choice when it comes to dating. “Having sex too soon clouds your judgment and makes it difficult to make an intelligent choice of partner,” Tessina says. Jumping into bed right away can hinder the possibility of getting to know each other since your focus is now on sex?— not on bonding in other (non-physical) ways. “If and when sex is right, it will happen. It's easy to have a one-night stand, but, if you want a relationship, you need to be more careful.”

It happened to her: “The last relationship I was in got physical really fast. I didn't think much about it or overanalyze it, but to be honest, things never really got off the ground intellectually or emotionally once we'd slept together. I really liked him on a lot of levels, but we never truly clicked if that makes sense.” Christina, Toronto, Canada

Waiting a while (at least several dates) before sleeping with someone gives you a chance to figure out how to be together in a way that works, or what Tessina refers to as forming some of the "infrastructure of a relationship"?— basically an interest in each other that is more than just physical and immediate. “Waiting to have sex gives you a chance to develop the friendship/partner aspect of your relationship,” she explains.

It happened to her: The times where I've waited to have sex have mostly seemed to boost the relationship. Not always, but more often than not, both the sex and the relationship seem stronger when I've taken some time to really get to know the person I'm going to sleep with.” Kirsty, Fort Worth, Texas

Sexual attraction won't go away if you get to know each other and let's face it, if it does, then that connection was pretty insubstantial to begin with. Plus, waiting a few dates can have its perks. “The suspense of abstaining can really up the intensity of sex when it finally does happen,” affirms Tessina. “If you eliminate the mystery too soon, you may also eliminate any future for this relationship.”

It happened to her: “I find that when I sleep with a guy right away, while it seems fun and adventurous, it can actually make sex less awesome in the long run. My current boyfriend and I waited a while to have sex because we were trying the just-friends thing first, and when we finally slept together, it was a lot more electric because of the build-up.” Ally, Chicago, Illinois

If you've been dating for a while, and you've had a chance to bond a little, go for it. “If the interest feels mutual and not one-sided, if you survived a disagreement and worked it out, if you feel mutual respect and caring, then you probably have enough foundation to take the risk of being sexual,” Tessina says.

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