Should You Go On Another Date?

On the fence about whether to see someone again? So were these singles—so we helped them decide. See if you can relate to these common dilemmas.

By Amy Spencer

e’ve all been there—hashing over the details of a date we’ve recently had, analyzing the interaction and consulting our friends, all in an attempt to answer one crucial question: Should I see this person again? Ultimately, of course, only you can decide whether you’re game for another rendezvous. Usually the concerns a single person has cluster around certain issues: Does it matter that you have nothing in common? Does it matter if the spark isn’t there right away? How many chances should you give someone before you give up and move on?

To help you decide what to do in these situations, we gathered questions from real singles
While bad kissing may seem like a deal-breaker, take heart: It’s probably just that you two need to sync up your smooching styles.
and brought them to the experts. Who knows? Maybe your own love-limbo question is answered below.

Q: I had a great second date with this very attractive woman, but the kiss was awful. Should I give her another chance?
A: While this may seem like a total deal-breaker, take heart: Most people aren’t bad kissers per se, it’s just that their smooching style differs from your own. And whether you’re, say, into deep, passionate kissing while she prefers softer pecks, know that getting your styles more in synch is entirely possible. “I’ve talked with so many couples about this issue, and I know it’s possible for any person to step up to the plate and learn to do what you like,” says Sharyn Wolf, CSW, a psychotherapist in New York and author of Guerrilla Dating Tactics. Who knows? Maybe she was fumbling under the pressure. Or maybe her ex-boyfriend actually preferred she smooch that way, and she assumes you’d like the same. To clue her into your preferences, the next time you’re canoodling, try saying something like “I noticed our kissing styles are pretty different. Want to try doing things a little differently and see what you think?” That way, she’ll think of it as experimenting rather than criticism—and may rise to the occasion. Also remember that all good relationships involve give and take. Maybe you want to try her style for a change, too.

Q: Recently I went out with a guy who was really sweet, but then he only gave the waitress a 2-percent tip, which was a huge turnoff. Is this an omen of things to come, and should I cut him loose?
A: Before you just assume he’s cheap, you may want to make sure his decision to stiff the waitress was deliberate. “Sometimes first dates can make someone nervous enough to make a mistake like that,” says Wolf. “So if you felt a generosity from him in general, then yes, you should give it one more try.” And if it turns out he’s still as stingy? Then you need to decide if you can live with a man who’s probably going to be tight with money in other areas. “Money habits rarely change,” says Wolf. Which means a future with him may mean vacationing in your backyard, getting “practical” gifts (“You said you needed a blender!”), and compensating for him when he doesn’t tip in the future. If you like to live your life more generously, then this might mean you should cash out and cut your losses.

Q: I’ve been on three dates with this guy, and we have great conversations, but almost nothing in common. He’s totally into politics, and I’m totally into pop culture. Is it even worth trying to make it work?
A: Actually, it’s totally worth it. “If you each have an interest in learning from each other, it can be a rich experience,” says Wolf. You’ll both become better, more well-rounded people from it—and if you do get a hankering to swap tabloid gossip, that’s what friends are for. And the best part is, this leaves the door open for you both to create a new common interest together. For your next date, do something that’s new to both of you: Try hiking, bowling, glass blowing, going to a photography exhibit together, hitting golf balls at the driving range, whatever. The point is, there’s more to life than politics and pop culture, and it should be a fun challenge to explore it together.

Q: I’m a huge joker, but on our first date, she didn’t laugh at any of my jokes. Should I try again?
A: Having a completely different sense of humor from your date is no laughing matter. “A long relationship requires a lot of laughter, and if she doesn’t find you funny now, you’re going to have a really hard time later,” says Wolf. And while it doesn’t look great for you two, don’t hang your judgment on one date, because you both may have been trying too hard. Is it possible that you were so nervous you were cracking too many jokes
Money habits rarely change. So if your date’s a stingy tipper, you can bet you’re in for a future of low-budget vacations and “practical” birthday presents.
and not listening to what she was saying? Is it possible she was too nervous to laugh, didn’t understand you were being funny, or wasn’t used to your dry sense of humor? If so, give her one more shot, but if things don’t click, maybe you should bail. After all, you deserve someone who appreciates your wit.

Q: After a third date, I brought the woman I’m seeing to meet my friends. They all said she was a little standoffish and rude. Are they seeing something I’m not?
A: Only time will tell. First off, is there anything that makes a person more anxious than meeting the inner circle? That’s a lot of pressure for someone who’s still trying to impress you, let alone your friends. “Sometimes people who are insecure or unsure of themselves will seem standoffish to people who don’t know them,” explains Catherine Cardinal, Ph.D., a couples’ counselor in Santa Monica, CA. Another point: It’s worth thinking about what your friends have to gain or lose by telling you this. “There are a thousand reasons why your friends may not want you with this girl,” says Wolf. They may be afraid to lose you as a poker partner. They may love that when you’re single, you’re more apt to get drunk and sing karaoke for their amusement. The point is, they may not be looking out for your best long-term love interests. “At this stage,” says Wolf, “focus on your feelings about her and yours alone.” So go on another date or twelve and let time reveal her true nature.

Q: This guy brought me to a party for our first date, but kept excusing himself to talk to other people, answer his cell phone, or text his friends. Is this a bad sign?
A: It certainly doesn’t bode well. Any person who doesn’t make an effort to focus on you during a date is probably either rude or just not that smitten. In either case, this may not be someone you should bend over backwards to see again. If he does call for another date, ask about his plans upfront to make sure your time together is one-on-one. If he whips out his cell tell him, “I’d really prefer you turn that off so we can actually get to know one another.” Then you can judge if you like his more focused self—or if it’s time to disconnect.

Q: During my first date with this guy, all he did was brag about how big his job is, how nice his car is, and how many celebrities he’s met. He may be a nice guy underneath all that, but is it worth trying to break through?
A: Ooh, this is a tough one. And the fact is, it’s going to take a second date to figure it out. On the one hand, “He sounds narcissistic and arrogant,” says Cardinal. But then again, “he’s obviously deeply insecure and probably very nervous,” says Wolf, “and that’s a lethal combination for a first date.” If you thought he was a plain old bragging jerk, you wouldn’t be asking if you should go on another date—you’d have already kicked him to the curb. So the fact that you’re asking shows you probably sensed there is more to him, and it might be worth giving him one more chance to show his true colors. Is it possible there was something about you that made him think he had something to prove? Like, say, you always date powerful, successful men? He may have felt he needed to live up to that. Next time, when he goes on about his fancy suit, stop him. Say, “Just for the record, money doesn’t really impress me, so you don’t have to mention it.” Or, suggest swapping embarrassing stories—and tell yours first. Then he may feel more comfortable letting his guard down. That’s when you’ll be able to tell whether a real relationship can thrive.

">Amy Spencer writes for Glamour, Maxim, Real Simple, and other publications.

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