How to Know if Your Date is Transgender
While you won't be able to know if your date is transgender unless they tell you, focus on being open-minded and considerate so you and your date have a great time! When you meet your date, keep in mind that everyone's body is different, so there are no clear-cut physical traits that will distinguish them. While it may be tempting, don't ask your date if they're transgender. This is personal information and you'll likely offend them by asking. Remember, trans people aren't trying to trick you. They just want what everyone else wants, to be accepted for who they are!
Be aware that there are no clear-cut physical signs that you can rely on. You'll never be able to identify a trans person through physical attributes alone. People's bodies are incredibly diverse, and a single physical characteristic won't say much about a person one way or the other. Moreover, genital reconstructive surgery has come such a long way that many who undergo it (not all trans people do) are indistinguishable from those who haven't. Avoid asking your date if they are transgender. You will likely offend them either way. If the person you're talking to is trans, they may not have been ready to tell you. If they're not, and if they have negative feelings towards trans people, they'll feel insulted. Odds are, asking them is one-way ticket to them doing one of two things: Worst case? Throwing a drink in your face. Best case? Just walking away. Disclosing can be very painful and even dangerous for them. This is their information to tell, when they feel safe enough with you. In short, they aren't required to tell you, nor should they have to if they don't want to. At any rate, they will likely tell you before intimate contact is had. Examine your own bias. If you're wondering if your date is trans, you might be harboring some negative stereotypes in your mind that are not based in reality or you don't want to be mixed up with a trans person. Moreover, your reaction to your date if they are trans, based on your misunderstanding and bias, can be devastating to someone who already faces societal rejection and abuse. If they are trans, they are no less of a person and they should be treated the same way. If you find yourself dealing with fear over finding out your date is trans, read How to Deal With Transphobia and How to Respect a Transgender Person. It may help you understand what they're going through and how they feel. Stop worrying and relax. There are many other things to worry about that actually warrant worry, such as STDs. If the person is trans, wait for them to tell you. If everything else has gone well up to that point, you can cross that bridge when you get there. What's the problem if you're just in the dark for right now? If things progress, you will eventually find out. At that point, one of two things will happen: the relationship will continue or it won't. It is not the end of the world. Simply enjoy the person for right now; if it pans out, great. If it doesn't, that's okay too. Keep an open mind. There are many happy endings that began with a date where one person did not know the other person was trans: It Happened to Me: I Told My Boyfriend I Was Born a Boy and Falling in Love with a Transgender Man are two prominent examples. Sexuality is fluid. You may find yourself attracted to this person despite their assigned sex. That is normal and absolutely fine. Listen to your emotions and how this person makes you feel. You may find that they're such a good person it doesn't matter. However, it's important to remember that transgender people are their gender. They are not "men pretending to be women", "women pretending to be men", or anything else. They can have any physical characteristics, and not all have the ones of their assigned gender. Realize that they're not trying to trick you. Gender is in someone's heart, not in their underpants, and trans people transition so that they can be their authentic selves. Trans people's safety is at risk when they go out to date; they wouldn't fake it for fun. If a trans person wants to date you, they want to be accepted for who they are. All humans need to be social and experience flirtation, relationships, and love. Would you walk up to that cute girl at the bar and say, "I have serious commitment issues?" Didn't think so. They are doing absolutely nothing wrong by being present and engaging with you. If you do not accept transgender people, mention it clearly without elaboration. For example, "Just so you know, I don't like trans/LGBT people. If that's a dealbreaker for you, you should walk away." This way they (and any trans allies) can walk away. Don't elaborate on your feelings; you might really hurt them, and/or have a drink thrown in your face. Know the difference between sexual orientation and gender identity. For the record, it's not gay people that become transgender to become straight. In fact, it's often the opposite. Sexual orientation and gender identity are completely different. Think of it this way: sexual orientation involves who you want to go to bed with. Gender identity, on the other hand, involves who you go to bed as. Understand why a trans person might be afraid to share this information with you. Trans people often face ostracism, bullying, abuse, and even violence. It can be hard to tell a safe person from a dangerous one. Especially if they have a history of being hurt, a trans person may be very cautious about coming out to you, because they don't want to risk their life. If the world were a more understanding place, this wouldn't be an issue. They would be happy to share this aspect of their lives with you. Let them tell you on their own time. If the relationship is going to progress, you will find out. Whether they tell you verbally or you find out physically, it'll happen. And that's fine. You just have to know how it makes you feel and what you'll want to do from there. That's it. It's not gross, it's not bad. It just is. When you hear talk of, "There's something you don't know about me," this could be a telltale sign. Comfort them, letting them know you accept them, whatever that thing is. Ask them why they're hesitant to tell you and don't let them drop it. You need to know for the relationship to progress from here. They're practically there anyway. They just need a little supportive nudging. Figure out how you feel. Dating a trans person isn't always a sign that anything is different about you. (For example, if you consider yourself a lesbian, and you date a trans woman, you're still a lesbian.) A trans person's gender is the one in their heart, and that's what counts when you consider your orientation. However, if you're dating someone of a different gender than what you're used to, it may mean that it's time to re-evaluate and experiment. It's possible that you are bisexual or pansexual. You might also like words such as "heteroflexible" or "homoflexible" (straight/gay with exceptions) if you usually date people of one gender. Remember that sexuality is fluid. The idea that there are only men and women, straight and gay is not how human sexuality works. What's more, there is no prize you win for being straight. Updating your self-concept may be called for in this situation. And that is more than okay. 
Be aware that there are no clear-cut physical signs that you can rely on. Avoid asking your date if they are transgender. Examine your own bias. Stop worrying and relax. Keep an open mind. Realize that they're not trying to trick you. Know the difference between sexual orientation and gender identity. Understand why a trans person might be afraid to share this information with you. Let them tell you on their own time. Figure out how you feel. 