It’s cool when a friend wants to hook you up — for one thing, you can be pretty sure the guy’s not a loser. But, there’s a higher awkwardness potential if it doesn’t work out, so ask your matchmaking pal these questions first (consider this your bad-date insurance).

“Why do you think we’d be a good match?”

Many people assume that since they get along with both of you, you’ll be into each other, too — not always true. This question forces her to articulate your commonalities. Watch out if your friend seems hard-pressed to answer.

“What’s his recent dating history like?”

If he just got out of a long-term thing or hasn’t had a girlfriend in several years, that might mean he’s not looking for anything serious at the moment. That’s fine if you want a casual relationship, too. But, you should know what you’re getting into up front.

“How would you describe me to someone?”

Your friend’s response reveals the type she thinks you’d go for. For instance, she replies that you’re sweet and quiet… but in fact, you like a guy who’s edgy. The one she’d pick for you might be way too understated (read: boring). It also clues you in to what she’s told your prospective date about you.

His ex-girlfriend is still in the picture

Some of us are just incapable of moving on. Kidding. Men get sentimental too, you know. But that’s just about it most of the time: nostalgia. Sure, we get all fuzzy when we remember the good times, but soon after, the issues that made us call it quits come up and we realize why we got off that particular love bus in the first place. If it really bothers you that he’s still in touch with his ex, then by all means, calmly assert yourself. Be honest and talk it through. If your boyfriend includes you in the relationship with his ex and displays affection toward you in front of her, you have nothing to worry about.

Oh So Random discovers the qualities a guy looks for before committing to an exclusive relationship.

• You give good ear. Men want a girl who shows enthusiasm about stuff that’s important to him, from his job to his fantasy NBA team. Making eye contact and asking questions convey that genuine interest.
• You do your own thing. Your independence is one of your sexiest assets, to don’t let hobbies and passions fall by the wayside. Maintaining your routine shows you’re interesting and confident — attributes no dude can resist.
• You laugh. Often. Guys don’t want you to be one of those overly giggly chicks, but they do want you to think they’re funny. Laughing at a man’s jokes makes him feel good and proves you’re carefree.
• You call him out. If your boyfriend is habitually late or never calls when he says he will, he may be testing to see if you’ll point out that he’s acting like a jerk. The right man values a woman who respects herself enough to give him a challenge — and inspire him to step up.

When you have an insanely hectic schedule, your connection needs extra attention. Here’s how to carve out some together-time.

✔ Speed-date each other. Meet for a quick drink before heading out with separate group of friends, says relationship therapist Krista Bloom, PhD. “It’s a good way to touch base and keep things grounded,” she adds.

✔ Plan a mid-week vacation day. “When your work schedules permit it, take a day off together,” suggests Ellen Kenner, Ph, host of The Rational Basis of Happiness. Make a day trip out of it — for example, scout out a new hotspot or resto. “Scheduling mutual downtime will put you emotionally in sync,” says Kenner.

✔ Set the alarm early. Of one of you leaves while the other continues to snooze and you don’t see each other until the evening, wake up twenty (20) minutes before you really need to. You can cuddle, talk, or massage each other. It’ll help you feel close when you do go your separate ways.